Water → HCID 58405155, compound

HRID 237261Notes

Reaction equation

HRID 237261 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH3:21])=[C:6]([CH:18]=1)[O:7][CH:8]1[CH2:11][N:10](C(=O)C(F)(F)F)[CH2:9]1.C([O-])([O-])=O.[K+].[K+].O>CO.C(Cl)Cl>[NH3:10].[CH3:6][OH:7].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH:20]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH3:21])=[C:6]([CH:18]=1)[O:7][CH:8]1[CH2:11][NH:10][CH2:9]1

Participants

7

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 87365918HCID 87365918, compound

Product 2

HCID 21705897Ammonia methanolHCID 58405155HCID 58405155, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To the title compound of Step B in MeOH (4 mL) was added K2CO3 (0.10 g, 0.72 mmol). After 15 h, H2O was added and the mixture extracted with EtOAc (2×). The combined organics were dried and concentrated. Silica gel chromatography (1-7 2M NH3/MeOH in CH2Cl2) gave 0.75 g (68% yield) of the title compound. MS (ESI): mass calcd. for C17H18ClNO2, 303.10; m/z found, 304.1 [M+H]+. 1H NMR (CDCl3): 7.38-7.31 (m, 4H), 7.28-7.24 (m, 1H), 6.72 (dd, J=8.6, 2.4 Hz, 1H), 6.67 (d, J=8.6 Hz, 1H), 6.55 (d, J=2.4 Hz, 1H), 5.23 (q, J=6.4 Hz, 1H), 4.99-4.93 (m, 1H), 3.95-3.81 (m, 4H), 1.66 (d, J=6.5 Hz, 3H).

Workup

  1. extractionthe mixture extracted with EtOAc (2×)
  2. customThe combined organics were dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c63c2ad3c0d241d5809539da9410f0d9
Source dataset
uspto-grants-2014_02
Patent number
US08642583B2

Reaction notes

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