Water → HCID 58204189, compound

HRID 1849235Notes

Reaction equation

HRID 1849235 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, 1 H), 7.51-7.46 (m, 1H), 7.19-7.00 (m, 4H), 6.50 (d, J=8.8 Hz, 1 H), 4.19 (t, J=4.4 Hz, 2 H), 3.66-3.65 (m, 2 H), 3.07 (t, J=4.8 Hz, 2H), 0.93-2.89 (m, 2 H), 2.13 (s, 3 H), 2.03 (s, 2 H), 1.29-1.24 (m, 6 H). ESI-MS: m/z=537 [M+H+]

Workup

  1. customThe solid was collected

Sources & evidence

ORD record
ord-8a57d584d3204be890ad140bf7a3773a
Source dataset
uspto-grants-2015_02
Patent number
US08952043B2

Reaction notes

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