Ammonia → HCID 71539919, compound

HRID 1915842Notes

Reaction equation

HRID 1915842 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]([CH3:44])[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>C(O)(C(F)(F)F)=O.C(Cl)Cl>[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]([CH3:44])[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 86680060HCID 86680060, compound

Product 1

HCID 71539919HCID 71539919, compoundYield 73.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl (R)-4-(4-(5-(tert-butoxycarbonylamino)-2-(2,6-difluorophenyl)thiazole-4-carboxamido)-1-methyl-1H-pyrazol-5-yl)-2-methylpiperazine-1-carboxylate (80 mg, 0.126 mmol) in TFA (1 mL) and DCM (4 mL) was stirred at ambient temperature for 3 hours. The pH of the mixture was adjusted to about 8˜9 by addition of ammonia and concentrated under reduced pressure to give a residue. The residue was purified by preparative HPLC to afford 102 (40 mg, 73%). 1H NMR (500 MHz, CDCl3) δ (ppm): 8.48 (s, 1H), 8.33 (s, 1H), 7.69 (s, 1H), 7.30-7.36 (m, 1H), 7.03-7.07 (m, 2H), 6.14-6.17 (m, 2H), 3.78 (s, 3H), 3.53-3.48 (m, 1H), 2.90-3.34 (m, 6H), 1.32 (d, J=6.5 Hz, 3H); MS (ESI) m/z=434 (M+1+).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto give a residue
  3. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-32eafacc0bf74b51b6e3eb9611df3463
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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