Hydrochloric Acid → HCID 86666543, compound

HRID 1400013Notes

Reaction equation

HRID 1400013 reaction equation
Cl.C(OC(=O)[NH:8][C@H:9]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:10][NH:11][C:12]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[C:20]([Cl:28])[CH:19]=2)[N:15]=[CH:14][N:13]=1)(C)(C)C>C(Cl)Cl>[ClH:28].[Cl:28][C:20]1[CH:19]=[C:18]([C:16]2[N:15]=[CH:14][N:13]=[C:12]([NH:11][CH2:10][C@@H:9]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[NH2:8])[CH:17]=2)[CH:23]=[CH:22][C:21]=1[C:24]([F:26])([F:25])[F:27]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 51035781HCID 51035781, compound

Product 1

HCID 86666543HCID 86666543, compoundYield 156.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A HCl solution (2 M in Et20, 1.01 mL) was added to tert-butyl[(1R)-2-({6-[3-chloro-4-(trifluoromethyl)phenyl]pyrimidin-4-yl}amino)-1-phenylethyl]carbamate (200 mg, 0.41 mmol) in CH2Cl2 (4 mL). The reaction mixture was stirred at rt overnight. The precipitate was filtered and washed with Et2O to yield the title compound (138 mg, 79%). MS (ESI): mass calcd. for C19H16ClF3N4, 392.10; m/z found, 393.1 [M+H]+. 1H NMR (CD3OD): 8.85 (s, 1H), 8.13 (s, 1H), 8.04 (d, J=8.3 Hz, 1H), 7.93 (d, J=8.3 Hz, 1H), 7.56-7.44 (m, 5H), 7.15 (s, 1H), 4.74-4.70 (m, 1H), 4.26 (dd, J=14.1, 7.1 Hz, 1H), 4.14 (dd, J=14.4, 7.1 Hz, 1H).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with Et2O

Sources & evidence

ORD record
ord-d50ecb3b593e4850a2deba0c4ec73a04
Source dataset
uspto-grants-2014_12
Patent number
US08906914B2

Reaction notes

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