Methyl chloroformate → HCID 23652792, compound

HRID 1094497Notes

Reaction equation

HRID 1094497 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[F:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]2[C:25]3[C:20](=[CH:21][C:22]([CH2:26][C:27]4[CH:32]=[C:31]([NH2:33])[N:30]=[CH:29][N:28]=4)=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)=[O:15])=[CH:9][C:8]=1[C:34]([F:37])([F:36])[F:35]>C(Cl)Cl.N1C=CC=CC=1.CCOC(C)=O.O>[CH3:5][O:4][C:2](=[O:3])[NH:33][C:31]1[CH:32]=[C:27]([CH2:26][C:22]2[CH:23]=[CH:24][C:25]3[C:20](=[CH:19][CH:18]=[CH:17][C:16]=3[C:14](=[O:15])[NH:13][C:10]3[CH:11]=[CH:12][C:7]([F:6])=[C:8]([C:34]([F:37])([F:36])[F:35])[CH:9]=3)[CH:21]=2)[N:28]=[CH:29][N:30]=1

Participants

7

Reactant 2

HCID 6586Methyl chloroformateHCID 23652721HCID 23652721, compound

Product 1

HCID 23652792HCID 23652792, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.4 ml (5 mMol) methyl chloroformate are added to a solution of 54 mg (0.123 mMol) 6-(6-amino-pyrimidin-4-ylmethyl)-naphthalene-1-carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amide in 1 ml CH2Cl2 and 1.5 ml pyridine. After 20 h, the solution is diluted with EtOAc and water, the aq. phase separated off and extracted twice with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Chromatography (Combi Flash; CH2Cl2→CH2Cl2/MeOH 92:8) gives the title compound: MS: [M+1]+=499; TLC (CH2Cl2/MeOH 85:15): Rf=0.54; 1H-NMR (DMSO-d6): δ ppm 10.86 (s, HN), 10.65 (s, HN), 8.69 (s, 1H), 8.30 (d, 1H), 8.13 (d, 1H), 8.03 (m, 2H), 7.90 (s, 1H), 7.74 (m, 2H), 7.58 (t, 1H), 7.50 (m, 2H), 4.22 (s, H2C), 3.64 (s, H3C).

Workup

  1. customthe aq. phase separated off
  2. extractionextracted twice with EtOAc
  3. washThe organic layers are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cf5667102d664262a21497ec791cd817
Source dataset
uspto-grants-2012_03
Patent number
US08133886B2

Reaction notes

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