Methyl iodide → HCID 25166709, compound

HRID 1177908Notes

Reaction equation

CI.[O:3]=[C:4]([N:22]1[CH2:27][CH2:26][N:25]([C:28](=[O:39])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[C:35]([F:38])([F:37])[F:36])[CH2:24][CH2:23]1)[CH2:5][NH:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][C:10]=1[OH:21])=[O:8].[C:40]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[O:3]=[C:4]([N:22]1[CH2:27][CH2:26][N:25]([C:28](=[O:39])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[C:35]([F:37])([F:38])[F:36])[CH2:24][CH2:23]1)[CH2:5][NH:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:11][C:10]=1[O:21][CH3:40])=[O:8]

Participants

Conditions

Temperature: 80 °C

Procedure

Methyl iodide (21 mg, 0.009 ml, 0.148 mmol) was added to a stirred solution of 3-hydroxy-biphenyl-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide (prepared by the method as described above) (51 mg, 0.1 mmol) and K2CO3 (20 mg, 0.144 mmol) in DMF (3 mL) and the resulting mixture was stirred at 80° C. for 2 hrs. The mixture was filtered, the filtrate was diluted with cold water and filtered the solid precipitated out, dried to afford 41 mg (78.84% yield) of 3-methoxy-biphenyl-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. 1H NMR: (DMSO-d6): δ 8.8-8.7 (bs, 1H), 8.04-7.98 (bs, 1H), 7.88-7.74 (dd, 4H), 7.72-7.64 (t, 1H), 7.58-7.46 (m, 3H), 7.46-7.34 (m, 3H), 4.32-4.18 (bs, 1H), 4.04 (s, 3H), 3.8-3.66 (bd, 2H), 3.66-3.54 (bt, 3H), 3.22-3.04 (bs, 1H).

Workup

customprepared by the method
filtrationThe mixture was filtered
additionthe filtrate was diluted with cold water
filtrationfiltered the solid
customprecipitated out
customdried

Sources & evidence

ORD record: ord-5fb2962ff322436985f4eebafc0f460a
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842696B2

Reaction notes

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