Diisopropylethylamine → HCID 44628831, compound

HRID 2189488Notes

Reaction equation

HRID 2189488 reaction equation
C(N(C(C)C)CC)(C)C.[F:10][C:11]([F:23])([F:22])[C:12]1[CH:13]=[C:14]([S:18](Cl)(=[O:20])=[O:19])[CH:15]=[CH:16][CH:17]=1.Cl.[CH:25]1([NH:28][C:29](=[O:42])[C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]3[CH2:37][CH2:38][NH:39][CH2:40][CH:41]=3)[N:31]=2)[CH2:27][CH2:26]1>ClCCl>[CH:25]1([NH:28][C:29]([C:30]2[N:31]=[C:32]([C:36]3[CH2:37][CH2:38][N:39]([S:18]([C:14]4[CH:15]=[CH:16][CH:17]=[C:12]([C:11]([F:23])([F:22])[F:10])[CH:13]=4)(=[O:20])=[O:19])[CH2:40][CH:41]=3)[CH:33]=[CH:34][CH:35]=2)=[O:42])[CH2:26][CH2:27]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27332503-(Trifluoromethyl)benzenesulfonyl chlorideHCID 67218212HCID 67218212, compound

Product 1

HCID 44628831HCID 44628831, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diisopropyl ethyl amine (66 ml, 0.36 mmol) and 3-(trifluoromethyl)benzene sulfonyl chloride (6) (44 mg, 0.18 mmol, Aldrich) were sequentially added to a suspension of compound 5 (50 mg, 0.18 mmol) in dichloromethane at 0° C. while stirring. The reaction was completed within 0.5 hour and the crude product was purified without work-up on CombiFlash® with a gradient of 50-100% EtOAc in hexane to provide the title compound 7 as a white solid (50 mg, yield 64%). 1H NMR (400 MHz, CD3OD): δ 8.15 (m, 2H), 8.02-7.83 (m, 4H), 7.67 (dd, 1H, J=1.2, 7.6 Hz), 6.78 (m, 1H), 3.92 (m, 2H), 3.45 (m, 2H), 2.87 (m, 1H), 2.77 (m, 2H), 0.86 (m, 2H), 0.70 (m, 2H); MS: 452 (M+H+), 474 (M+Na).

Workup

  1. customthe crude product was purified without work-up on CombiFlash® with a gradient of 50-100% EtOAc in hexane

Sources & evidence

ORD record
ord-545d542b24914fbd9b35dd6f13e76d38
Source dataset
uspto-grants-2012_12
Patent number
US08324249B2

Reaction notes

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