Water → HCID 58203993, compound

HRID 2385887Notes

Reaction equation

HRID 2385887 reaction equation
[NH:1]1[CH2:4][CH:3]([NH:5][C:6]2[CH:7]=[CH:8][C:9]3[O:18][CH2:17][CH2:16][C:15]4[CH:14]=[C:13]([C:19]5[N:20]([C:24]6[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=6[F:31])[N:21]=[CH:22][N:23]=5)[S:12][C:11]=4[C:10]=3[N:32]=2)[CH2:2]1.[CH3:33][S:34](Cl)(=[O:36])=[O:35].CCN(C(C)C)C(C)C.O>C1COCC1>[F:31][C:25]1[CH:26]=[C:27]([F:30])[CH:28]=[CH:29][C:24]=1[N:20]1[C:19]([C:13]2[S:12][C:11]3[C:10]4[N:32]=[C:6]([NH:5][CH:3]5[CH2:4][N:1]([S:34]([CH3:33])(=[O:36])=[O:35])[CH2:2]5)[CH:7]=[CH:8][C:9]=4[O:18][CH2:17][CH2:16][C:15]=3[CH:14]=2)=[N:23][CH:22]=[N:21]1

Participants

6

Reactant 4

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 58203940HCID 58203940, compound

Product 1

HCID 58203993HCID 58203993, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Azetidin-3-yl-{2-[2-(2,4-difluoro-phenyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-6-oxa-1-thia-10-aza-benzo[e]azulen-9-yl}-amine (452 mg, 1.0 mmol), Methanesulfonyl chloride (136 mg, 1.2 mmol), DIPEA (260 mg, 2.0 mmol) was dissolved in THF (10 mL). The reaction mixture was stirred at room temperature (r.t.) for 1 hour. LC-MS indicated the reaction was completed. To the reaction mixture was added 20 mL of water, the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and concentrated to dryness. The crude was purified by pre-HPLC to afford 363 (57.2 mg, yield: 11%). 1HNMR (DMSO-d6, 400 MHz): δ 9.50 (s, 1H), 8.72 (s, 1H), 8.31 (s, 1H), 7.97-7.91 (m, 2H), 7.77-7.72 (m, 2H), 7.48-7.43 (m, 2H), 7.15 (s, 1H), 6.99 (s, 1H), 6.72 (d, J=4.4 Hz, 1H), 4.31 (s, 2H), 3.86 (s, 2H), 3.33 (s, 2H), 3.15 (s, 2H), 2.75 (s, 6H). ESI-MS: m/z=531 [M+H+]

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated to dryness
  4. customThe crude was purified by pre-HPLC

Sources & evidence

ORD record
ord-4bba27222aef4309a08c980390548715
Source dataset
uspto-grants-2012_09
Patent number
US08263633B2

Reaction notes

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