Sodium Bicarbonate → HCID 10232267, compound

HRID 1835303Notes

Reaction equation

[F:1][C:2]([F:42])([F:41])[C:3]1[CH:4]=[C:5]([CH:34]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:36]=1)[CH2:6][N:7]([CH3:33])[C:8](=[O:32])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12]([N:22]2[CH2:27][CH2:26][N:25]([C:28](=[O:31])[CH2:29]Br)[CH2:24][CH2:23]2)=[N:11][CH:10]=1.C(=O)(O)[O-:44].[Na+]>CN1CCCC1=O>[F:1][C:2]([F:42])([F:41])[C:3]1[CH:4]=[C:5]([CH:34]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:36]=1)[CH2:6][N:7]([CH3:33])[C:8](=[O:32])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12]([N:22]2[CH2:27][CH2:26][N:25]([C:28](=[O:31])[CH2:29][OH:44])[CH2:24][CH2:23]2)=[N:11][CH:10]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 0.12 g (0.18 mmol) N-(3,5-bis-trifluoromethyl-benzyl)-6-(4-bromoacetyl-piperazin-1-yl)-N-methyl-4-o-tolyl-nicotinamide, 1.2 ml 1-methyl-2-pyrrolidone and 0.2 ml half-saturated aqueous sodium bicarbonate solution was stirred at 100° C. over night. After cooling to room temperature and dilution with water the mixture was extracted with five portions of tert-butyl methyl ether. The combined organic extracts were dried with sodium sulfate, concentrated and dried in vacuo (0.5 mbar) at 70°. Flash column chromatography afforded 71 mg (64%) of the title compound as a white solid.

Workup

temperatureAfter cooling to room temperature
extractiondilution with water the mixture was extracted with five portions of tert-butyl methyl ether
dry with materialThe combined organic extracts were dried with sodium sulfate
concentrationconcentrated
customdried in vacuo (0.5 mbar) at 70°

Sources & evidence

ORD record: ord-e31d0fb2813643e8a8d8d927a3e33d48
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06770637B2

Reaction notes

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