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Hydrochloric Acid → 5-(1-Piperidin-4-yl-1H-pyrazol-4-yl)-3-(7-trifluoromethoxy-isoquinolin-3-yl)-pyridin-2-ylamine trihydrochloride

HRID 1926262
Notes
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Reaction equation

HRID 1926262 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH:18]=[C:17]([C:19]3[CH:20]=[N:21][C:22]([NH2:34])=[C:23](B4OC(C)(C)C(C)(C)O4)[CH:24]=3)[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C.[F:35][C:36]([F:57])([F:56])[O:37][C:38]1[CH:47]=[C:46]2[C:41]([CH:42]=[C:43](OS(C(F)(F)F)(=O)=O)[N:44]=[CH:45]2)=[CH:40][CH:39]=1.C(=O)([O-])[O-].[K+].[K+].[ClH:64]>COCCOC.O.C(Cl)Cl.C(OCC)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[ClH:64].[ClH:64].[ClH:64].[NH:8]1[CH2:9][CH2:10][CH:11]([N:14]2[CH:18]=[C:17]([C:19]3[CH:24]=[C:23]([C:43]4[N:44]=[CH:45][C:46]5[C:41]([CH:42]=4)=[CH:40][CH:39]=[C:38]([O:37][C:36]([F:35])([F:57])[F:56])[CH:47]=5)[C:22]([NH2:34])=[N:21][CH:20]=3)[CH:16]=[N:15]2)[CH2:12][CH2:13]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 534879604-[4-[6-Amino-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridin-3-yl]pyrazol-1-yl]piperidine-1-carboxylic acid tert-butyl esterHCID 86633143Trifluoromethanesulfonic acid 7-trifluoromethoxyisoquinolin-3-yl ester

Product 1

HCID 86633141
5-(1-Piperidin-4-yl-1H-pyrazol-4-yl)-3-(7-trifluoromethoxy-isoquinolin-3-yl)-pyridin-2-ylamine trihydrochloride

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-{4-[6-amino-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-3-yl]-pyrazol-1-yl}-piperidine-1-carboxylic acid tert-butyl ester (BB3) (75 mg, 0.16 mmol), trifluoromethanesulfonic acid 7-trifluoromethoxyisoquinolin-3-yl ester (69 mg, 0.19 mmol), potassium carbonate (66 mg, 0.48 mmol), Pd(PPh3)4 (18 mg, 0.016 mmol) in DME (1.5 mL) and H2O (0.5 mL) was evacuated and refilled with N2 (3×), then it was heated at 100° C. for 30 min using the microwave reactor. The reaction mixture was diluted with EtOAc (30 mL), washed with brine (10 mL), and dried over anhydrous sodium sulfate. The residue was purified by silica gel chromatography (Hex.:EtOAc=30:70→15:85) to give a yellow solid. This material was dissolved in DCM (2 mL) and treated with 1M HCl in diethyl ether (3 mL). The resulting mixture was stirred at room temperature overnight. The title compound was collected by filtration as a yellow solid and washed with DCM. MS (ES+): m/z=455.12 [MH+].

Workup

  1. customwas evacuated
  2. additionrefilled with N2 (3×)
  3. additionThe reaction mixture was diluted with EtOAc (30 mL)
  4. washwashed with brine (10 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe residue was purified by silica gel chromatography (Hex.:EtOAc=30:70→15:85)
  7. customto give a yellow solid
  8. filtrationThe title compound was collected by filtration as a yellow solid
  9. washwashed with DCM

Sources & evidence

ORD record
ord-cd55a761bce2442888ded348bf8c7d65
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08178668B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes