Water → HCID 58204189, compound

HRID 708058Notes

Reaction equation

HRID 708058 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([C:14]2[S:23][C:22]3[C:21]4[N:24]=[C:25]([N:28]5[CH2:33][C@H:32]([CH3:34])[NH:31][C@H:30]([CH3:35])[CH2:29]5)[CH:26]=[CH:27][C:20]=4[O:19][CH2:18][CH2:17][C:16]=3[CH:15]=2)=[N:12][CH:11]=[N:10]1.C(=O)([O-])[O-].[K+].[K+].[C:42](OC(=O)C)(=[O:44])[CH3:43].O>CN(C=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([C:14]2[S:23][C:22]3[C:21]4[N:24]=[C:25]([N:28]5[CH2:33][C@H:32]([CH3:34])[N:31]([C:42](=[O:44])[CH3:43])[C@H:30]([CH3:35])[CH2:29]5)[CH:26]=[CH:27][C:20]=4[O:19][CH2:18][CH2:17][C:16]=3[CH:15]=2)=[N:12][CH:11]=[N:10]1

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 57900099HCID 57900099, compound

Product 1

HCID 58204189HCID 58204189, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-[2-(2,4-Difluoro-phenyl)-2H-[1,2,4]triazol-3-yl]-9-((3R,5S)-3,5-dimethyl-piperazin-1-yl)-4,5-dihydro-6-oxa-1-thia-10-aza-benzo[e]azulene (150 mg, 0.3 mmol), potassium carbonate (84 mg, 0.6 mmol) in DMF (5 mL) was added acetic anhydride (0.3 mL) at −15° C. The mixture was slowly warmed to room temperature and stirred for 30 min. The reaction mixture was added 30 mL of water. The solid was collected to give 100 mg of 312. Yield=62%. 1H NMR (CDCl3, 400 MHz): δ8.03 (s, 1H), 7.51-7.46 (m, 1H), 7.19-7.00 (m, 4H), 6.50 (d, J=8.8 Hz, 1H), 4.19 (t, J=4.4 Hz, 2H), 3.66-3.65 (m, 2H), 3.07 (t, J=4.8 Hz, 2H), 0.93-2.89 (m, 2H), 2.13 (s, 3H), 2.03 (s, 2H), 1.29-1.24 (m, 6H). ESI-MS: m/z=537 [M+H+]

Workup

  1. customThe solid was collected

Sources & evidence

ORD record
ord-d7db2dfb413b45a4b6b5f2084c38477d
Source dataset
uspto-grants-2015_11
Patent number
US09175009B2

Reaction notes

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