Ethanol hydrochloride → HCID 90314175, compound

HRID 1524157Notes

Reaction equation

HRID 1524157 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[C:15]([S:20]([CH:23]4[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24]4)(=[O:22])=[O:21])=[N:16][CH:17]=[CH:18][CH:19]=3)=[CH:10][C:9]=2[F:35])=[N:6][CH:7]=1.[ClH:36].CCO>C(Cl)Cl>[ClH:36].[F:35][C:9]1[CH:10]=[C:11]([C:14]2[C:15]([S:20]([CH:23]3[CH2:27][CH2:26][NH:25][CH2:24]3)(=[O:22])=[O:21])=[N:16][CH:17]=[CH:18][CH:19]=2)[CH:12]=[CH:13][C:8]=1[C:5]1[N:6]=[CH:7][C:2]([NH2:1])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 21887872Ethanol hydrochlorideHCID 90314275HCID 90314275, compound

Product 1

HCID 90314175HCID 90314175, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution consisting of tert-butyl 3-(3-(4-(5-aminopyrazin-2-yl)-3-fluorophenyl)pyridin-2-ylsulfonyl)pyrrolidine-1-carboxylate (150 mg, 0.300 mmol) and DCM (10 mL) was added HCl/EtOH (5 N, 10 mL). The mixture was stirred at rt for 2 h, concentrated to dryness, and the resultant residue subjected to HPLC purification to give the title compound (67 mg, 52%). MS (ESI): mass calcd. For C19H18FN5O2S.HCl 399.12; m/z found, 400.1 [M+H]+. 1H NMR (300 MHz, DMSO-d6) δ 9.79 (br s, 1H), 9.42 (br s, 1H), 8.79 (d, J=4.6, 1H), 8.51-8.30 (m, 1H), 8.20-7.78 (m, 3H), 7.51-7.02 (m, 3H), 4.81 (dd, J=14.1, 7.6, 1H), 3.72 (s, 1H), 3.49-3.14 (m, 3H), 2.44-2.20 (m, 2H).

Workup

  1. concentrationconcentrated to dryness
  2. customthe resultant residue subjected to HPLC purification

Sources & evidence

ORD record
ord-98037acbfe0c455a84bab7d7dc4ff118
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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