Ammonia → HCID 86680106, compound

HRID 1915898Notes

Reaction equation

HRID 1915898 reaction equation
C(OC([NH:8][C:9]1[S:13][C:12]([C:14]2[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=2[F:21])=[N:11][C:10]=1[C:22]([NH:24][C:25]1[CH:26]=[N:27][N:28]([CH2:44][C:45]([F:48])([F:47])[F:46])[C:29]=1[N:30]1[CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[C@H:32]([CH3:43])[CH2:31]1)=[O:23])=O)(C)(C)C.N>Cl.CO.CO>[NH2:8][C:9]1[S:13][C:12]([C:14]2[C:15]([F:21])=[CH:16][CH:17]=[CH:18][C:19]=2[F:20])=[N:11][C:10]=1[C:22]([NH:24][C:25]1[CH:26]=[N:27][N:28]([CH2:44][C:45]([F:47])([F:48])[F:46])[C:29]=1[N:30]1[CH2:35][CH2:34][NH:33][C@H:32]([CH3:43])[CH2:31]1)=[O:23]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 86680107HCID 86680107, compound

Product 1

HCID 86680106HCID 86680106, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21893726Hydrochloride methanolSolvent

Procedure

A mixture of tert-butyl (R)-4-(4-(5-(tert-butoxycarbonylamino)-2-(2,6-difluorophenyl)thiazole-4-carboxamido)-1-(2,2,2-trifluoroethyl)-1H-pyrazol-5-yl)-2-methylpiperazine-1-carboxylate (82 mg, 0.12 mmol) in HCl/MeOH (10 mL) was stirred at ambient temperature for 20 hours. The reaction mixture was concentrated under reduced pressure to give a residue. The residue was diluted with MeOH (30 mL), neutralized with 28% ammonia solution, concentrated, and purified by preparative HPLC to afford 233 as a white solid (32 mg, 56%). 1H-NMR (500 MHz, CD3OD) δ (ppm): 7.69 (s, 1H), 7.51-7.45 (m, 1H), 7.17-7.12 (m, 2H), 4.84-4.78 (m, 2H), 3.22-3.17 (m, 1H), 3.05-2.86 (m, 6H), 1.08 (d, J=6 Hz, 3H); MS (ESI) m/z: 502 [M+H+].

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto give a residue
  3. concentrationconcentrated
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-f0d809a2408a4f3797fbbe6c0437bd1b
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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