Ammonia → HCID 86680067, compound

HRID 1915858Notes

Reaction equation

HRID 1915858 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]([CH3:45])[C:29]=1[N:30]1[CH2:35][C@H:34]([F:36])[CH2:33][C@H:32]([NH:37]C(=O)OC(C)(C)C)[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]([CH3:45])[C:29]=1[N:30]1[CH2:35][C@H:34]([F:36])[CH2:33][C@H:32]([NH2:37])[CH2:31]1)=[O:23]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 86680068HCID 86680068, compound

Product 1

HCID 86680067HCID 86680067, compoundYield 59.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21893726Hydrochloride methanolSolvent

Procedure

A mixture of tert-butyl (3S,5R)-1-(4-(5-(tert-butoxycarbonylamino)-2-(2,6-difluorophenyl)-thiazole-4-carboxamido)-1-methyl-1H-pyrazol-5-yl)-5-fluoropiperidin-3-ylcarbamate (100 mg, 0.15 mmol) in HCl/MeOH (10 mL) was stirred at ambient temperature for 20 hours and concentrated reduced pressure to give a residue. The residue was diluted with MeOH (10 mL), neutralized with 28% ammonia solution, and concentrated to give a crude product. The crude product was purified by preparative HPLC to give 127 (40 mg, 59%). 1H-NMR (500 MHz, CD3OD) δ (ppm): 7.51-7.49 (m, 2H), 7.17-7.12 (m, 2H), 4.95-4.86 (m, 2H), 3.75 (s, 3H), 3.31-3.25 (m, 3H), 2.97-2.90 (m, 1H), 2.31-2.23 (m, 1H), 1.64-1.48 (m, 1H); MS (ESI) m/z: 452 [M+H+].

Workup

  1. concentrationconcentrated reduced pressure
  2. customto give a residue
  3. concentrationconcentrated
  4. customto give a crude product
  5. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-84f015c662a44a328877c70d5fd191e7
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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