Water → HCID 58204153, compound

HRID 708059Notes

Reaction equation

HRID 708059 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:36](=O)([O-])[O-].[Cs+].[Cs+].CI.O>CN(C)C=O>[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]([CH3:36])[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 6328Methyl iodideHCID 10796Cesium carbonateHCID 57900099HCID 57900099, compound

Product 1

HCID 58204153HCID 58204153, compoundYield 68.8%

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 (100 mg, 0.2 mmol), Cesium carbonate (131 mg, 0.4 mmol) in N,N-dimethylformamide (5 mL) was added CH3I (0.025 mL, 0.4 mmol) at −15° C. The mixture was slowly warmed to room temperature and stirred for about 30 min. The reaction mixture was added 30 mL of water. The solid was collected to give 70 mg of 313. Yield=60%. 1H NMR (CDCl3, 400 MHz): δ8.02 (s, 1H), 7.51-7.46 (m, 1H), 7.11-6.97 (m, 4H), 6.46 (d, J=8.8 Hz, 1H), 4.18 (t, J=4.8 Hz, 2H), 3.85 (d, J=13.6 Hz, 2H), 3.08 (t, J=4.8 Hz, 2H), 2.59 (t, J=7.2 Hz, 2H), 2.26-2.19 (m, 4H), 1.14 (d, J=6.8 Hz, 6H). ESI-MS: m/z=509 [M+H+]

Workup

  1. customThe solid was collected

Sources & evidence

ORD record
ord-0ba95bf4c9cd40c4939224380b247e49
Source dataset
uspto-grants-2015_11
Patent number
US09175009B2

Reaction notes

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