Water → HCID 67228996, compound

HRID 600814Notes

Reaction equation

HRID 600814 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([O:13][C:14](=[O:27])[NH:15][C:16]1[C:25]2[CH2:24][CH:23]([NH2:26])[CH2:22][CH2:21][C:20]=2[CH:19]=[CH:18][CH:17]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(C(C)C)CC)(C)C.O>C(Cl)Cl>[CH2:6]([O:13][C:14](=[O:27])[NH:15][C:16]1[C:25]2[CH2:24][CH:23]([NH:26][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:22][CH2:21][C:20]=2[CH:19]=[CH:18][CH:17]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 67229016HCID 67229016, compound

Product 1

HCID 67228996HCID 67228996, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methanesulfonyl chloride (176 mg, 1.54 mmol) was added dropwise to a solution of the product from Example 20C (381 mg, 1.29 mmol) and diisopropylethylamine (332 mg, 2.57 mmol) in 15 mL CH2Cl2 at ambient temperature. The mixture was stirred 30 minutes, diluted with methylene chloride and poured into water. The separated organic phase was washed with 1N aq HCl, brine, dried (Na2SO4), filtered and concentrated under reduced pressure. Flash chromatography (4% CH3OH/CH2Cl2) yielded 281 mg (58%) of the title compound as a white amorphous solid. 1H NMR (DMSO-d6) δ 8.92 (s, 1H), 7.45-7.30 (m, 5H), 7.22 (d, J=7.1 Hz, 1H), 7.15 (m, 1H), 7.08 (t, J=7.5 Hz, 1H), 6.93 (m, 1H), 5.13 (s, 2H), 3.51 (m, 1H), 3.02 (m, 1H), 2.96 (s, 3H), 2.85 (m, 2H), 2.50 (m, 1H+ DMSO), 2.01 (m, 1H), 1.61 (m, 1H); MS (ESI+) m/z 375 (M+H)+.

Workup

  1. washThe separated organic phase was washed with 1N aq HCl, brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a8030e8082b146bb83bf5f6df73751b0
Source dataset
uspto-grants-2011_03
Patent number
US07902236B2

Reaction notes

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