Water → HCID 58203993, compound

HRID 708115Notes

Reaction equation

HRID 708115 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-e3c60a93866f4ecb9d7674908f7b7fbd
Source dataset
uspto-grants-2015_11
Patent number
US09175009B2

Reaction notes

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