Potassium Hydroxide → HCID 86592890, compound

HRID 984489Notes

Reaction equation

HRID 984489 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([S:11][C:12]3[CH:17]=[CH:16][C:15](/[CH:18]=[CH:19]/[C:20]([N:22]4[CH2:27][CH2:26][CH2:25][CH:24]([C:28]([O:30]CC)=[O:29])[CH2:23]4)=[O:21])=[C:14]([Cl:33])[C:13]=3[Cl:34])=[CH:8][CH:9]=2)[CH:4]=[CH:3]1.[OH-].[K+].[OH-].[Na+]>C(Cl)Cl>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([S:11][C:12]3[CH:17]=[CH:16][C:15](/[CH:18]=[CH:19]/[C:20]([N:22]4[CH2:27][CH2:26][CH2:25][CH:24]([C:28]([OH:30])=[O:29])[CH2:23]4)=[O:21])=[C:14]([Cl:33])[C:13]=3[Cl:34])=[CH:8][CH:9]=2)[CH:4]=[CH:3]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 86592891HCID 86592891, compound

Product 1

HCID 86592890HCID 86592890, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by the procedures described in Example 155, substituting the ethyl ester from Example 137 with ethyl ester from Example 337, and KOH with NaOH, to give a white solid. 1H NMR (d6-DMSO, 300 MHz) δ 1.29-1.45 (m, 1H), 1.45-1.78 (m, 2H), 1.78-2.02 (m, 1H), 2.20-2.40 (m, 1H), 2.82 (brt, J=10.5 Hz, 1H), 3.08 (brt, J=10.5 Hz, 1H), 3.80-4.07 (m, 2H), 3.86 (s, 3H), 4.38-4.50 (m, 1H), 6.42 (d, J=8.4 Hz, 1H), 6.54 (d, J=3.0 Hz, 1H), 7.19 (d, J=15.3 Hz, 1H), 7.32 (dd, J=1.8, 8.7 Hz, 1H), 7.48 (d, J=3.0 Hz, 1H), 7.64 (d, J=8.7 Hz, 1H), 7.67-7.77 (m, 2H), 7.87 (d, J=1.8 Hz, 1H). MS (ESI+) (M+H)+ at m/z 489, 491, 493. Anal. Calcd for C24H22Cl2N2O3S.0.56 CH2Cl2: C, 54.94; H, 4.34; N, 5.22. Found: C, 54.89; H, 4.44; N, 5.32.

Workup

  1. customto give a white solid

Sources & evidence

ORD record
ord-6669a930f0e945c4a8bc88bf4d343632
Source dataset
uspto-grants-2005_03
Patent number
US06867203B2

Reaction notes

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