4-(Trifluoromethyl)phenyl isocyanate → HCID 67285708, compound

HRID 869321Notes

Reaction equation

HRID 869321 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[N:14]([CH3:31])[C:15]([C:24]3[CH:29]=[CH:28][N:27]=[C:26]([NH2:30])[N:25]=3)=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([NH2:23])[CH:18]=3)[C:10]=2[C:9]1=[O:32])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:33]([C:36]1[CH:41]=[CH:40][C:39]([C:42]([F:45])([F:44])[F:43])=[CH:38][CH:37]=1)=[C:34]=[O:35]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[N:14]([CH3:31])[C:15]([C:24]3[CH:29]=[CH:28][N:27]=[C:26]([NH2:30])[N:25]=3)=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([NH:23][C:34]([NH:33][C:36]4[CH:37]=[CH:38][C:39]([C:42]([F:43])([F:44])[F:45])=[CH:40][CH:41]=4)=[O:35])[CH:18]=3)[C:10]=2[C:9]1=[O:32])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 67286102HCID 67286102, compound

Product 1

HCID 67285708HCID 67285708, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(3-amino-phenyl)-2-(2-amino-pyrimidin-4-yl)-1-methyl-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester (40 mg, 0.092 mmol) (prepared as described in Example 1) in dichloromethane (1 mL), 1-isocyanato-4-trifluoromethyl-benzene (0.014 mL, 0.101 mmol) was added. The mixture was stirred until disappearance of the starting material. The solvent was evaporated and the residued was suspended in diethylether and filtered to give 35 mg of 2-(2-Amino-pyrimidin-4-yl)-1-methyl-4-oxo-3-{3-[3-(4-trifluoromethyl-phenyl)-ureido]-phenyl}-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester. (y: 61%)

Workup

  1. customThe solvent was evaporated
  2. filtrationfiltered

Sources & evidence

ORD record
ord-e74eb5d5ab15418da779408a46f548e4
Source dataset
uspto-grants-2015_03
Patent number
US08969366B2

Reaction notes

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