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Hydrochloric Acid → Hydrochloric Acid

HRID 79134
Notes
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Reaction equation

HRID 79134 reaction equation
[Cl:1][C:2]1[C:7]2[N:8]([CH:35]3[CH2:39][CH2:38][CH2:37][CH2:36]3)[C:9]3[N:10]=[C:11]([NH:15][C:16]4[N:21]=[CH:20][C:19]([N:22]5[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]5)=[CH:18][CH:17]=4)[N:12]=[CH:13][C:14]=3[C:6]=2[CH:5]=[CH:4][N:3]=1.[ClH:40].O1CCOCC1>C(Cl)Cl.CCOCC>[Cl:1][C:2]1[C:7]2[N:8]([CH:35]3[CH2:39][CH2:38][CH2:37][CH2:36]3)[C:9]3[N:10]=[C:11]([NH:15][C:16]4[CH:17]=[CH:18][C:19]([N:22]5[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]5)=[CH:20][N:21]=4)[N:12]=[CH:13][C:14]=3[C:6]=2[CH:5]=[CH:4][N:3]=1.[ClH:40]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 58299799tert-Butyl 4-(6-((8-chloro-9-cyclopentyl-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]-pyrimidin-2-yl)amino)-3-pyridinyl)-1-piperazinecarboxylate

Product 2

HCID 313Hydrochloric AcidYield 100%HCID 58299601HCID 58299601, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Compound 197 (0.173 g, 0.315 mmol) was dissolved in 10 mL of DCM and to this was added 4N HCl in dioxane (1.97 mL, 7.88 mmol). The solution was stirred at room temperature overnight and then concentrated under vacuum to give a yellow solid. The solid obtained was sonicated in Et2O and a yellowish solid was collected on filter paper to give compound 190 as an HCl salt (0.164 g, 100%). 1H NMR (500 MHz, DMSO-d6) δ 10.56 (1 H, br. s.), 9.42 (1 H, s), 8.87 (2 H, br. s.), 8.28 (1 H, d, J=4.9 Hz), 8.19 (1 H, d, J=5.1 Hz), 8.09 (1 H, d, J=2.9 Hz), 7.97 (1 H, d, J=9.0 Hz), 7.75 (1 H, dd, J=9.3, 2.0 Hz), 5.96-6.07 (2 H, m, J=9.2, 8.9, 8.8, 8.8 Hz), 3.37-3.43 (4 H, m), 3.26-3.33 (4 H, m), 2.54-2.65 (2 H, m), 2.01-2.12 (4 H, m), 1.66-1.77 (2 H, m) ppm; LCMS-ESI (POS), M/Z, M+1: Found 449.2.

Workup

  1. concentrationconcentrated under vacuum
  2. customto give a yellow solid
  3. customThe solid obtained
  4. customa yellowish solid was collected
  5. filtrationon filter paper

Sources & evidence

ORD record
ord-2f4dc75a7bce43f790e903cf328d85b7
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08841312B2

Reaction notes

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