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Triethylamine → HCID 178434276, compound

HRID 711110
Notes
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Reaction equation

HRID 711110 reaction equation
Cl.[CH:2]([N:5]1[C:9]2[C:10](=[O:19])[NH:11][C:12]3([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[CH2:13][C:8]=2[CH:7]=[N:6]1)([CH3:4])[CH3:3].[CH3:20][C:21]1[C:29]2[C:24](=[C:25]([CH3:33])[CH:26]=[C:27]([C:30](O)=[O:31])[CH:28]=2)[NH:23][N:22]=1.C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>CN(C)C=O.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[CH3:20][C:21]1[C:29]2[C:24](=[C:25]([CH3:33])[CH:26]=[C:27]([C:30]([N:16]3[CH2:17][CH2:18][C:12]4([NH:11][C:10](=[O:19])[C:9]5[N:5]([CH:2]([CH3:4])[CH3:3])[N:6]=[CH:7][C:8]=5[CH2:13]4)[CH2:14][CH2:15]3)=[O:31])[CH:28]=2)[NH:23][N:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 674915351'-Isopropyl-4',6'-dihydrospiro[piperidine-4,5'-pyrazolo[3,4-c]pyridin]-7'(1'H)-one hydrochloride2×HCID 178434277HCID 178434277, compound

Product 1

HCID 178434276HCID 178434276, compoundYield 25.2%

Reagents, catalysts & solvents

3
HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1′-isopropyl-4′,6′-dihydrospiro[piperidine-4,5′-pyrazolo[3,4-c]pyridin]-7′(1′H)-one hydrochloride salt (Intermediate 2, 430 mg, 1.3 mmol) and 3,7-dimethyl-1H-indazole-5-carboxylic acid (306 mg, 1.6 mmol) in dimethylformamide (2 mL) was added triethylamine (0.75 mL, 5.4 mmol), 4-dimethylaminopyridine (33 mg, 0.37 mmol), and 1-propanephosphonic acid cyclic anhydride (0.52 mL, 1.74 mmol, 50% solution in ethyl acetate), and the reaction mixture was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo, taken up in ethyl acetate and washed with saturated aqueous sodium bicarbonate. The organic layer was dried over sodium sulfate, filtered, and concentrated to a solid. The solid was purified via flash column chromatography (0-15% methanol/dichloromethane) to afford a glassy solid. The glassy solid was stirred in ethyl acetate for 16 hours and the resulting solid collected by vacuum filtration to afford the desired product as a white solid (138 mg). +ESI (M+H) 421.0; 1H NMR (400 MHz, CD3OD, δ): 7.65 (s, 1H) 7.42 (s, 1H) 7.21 (s, 1H) 5.50 (m, 1H) 3.95 (br. s., 1H) 3.50-3.62 (br. s., 3H) 2.97 (s, 2H) 2.56 (m, 6H) 1.83 (br. s., 4H) 1.44 (d, 6H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washwashed with saturated aqueous sodium bicarbonate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to a solid
  6. customThe solid was purified via flash column chromatography (0-15% methanol/dichloromethane)
  7. customto afford a glassy solid
  8. filtrationthe resulting solid collected by vacuum filtration

Sources & evidence

ORD record
ord-c302c3b6c384424cb089e0e9977b7602
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09181252B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes