Ethyl isocyanate → N-[5-(3-{[(ethylamino)carbonyl]amino}phenyl)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide

HRID 18424Notes

Reaction equation

HRID 18424 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[CH2:13][CH:12]([NH:17][S:18]([CH:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])[CH2:11]3)[CH:5]=[CH:6][CH:7]=1.C(N(C(C)C)CC)(C)C.[CH2:33]([N:35]=[C:36]=[O:37])[CH3:34]>ClCCl>[CH2:33]([NH:35][C:36]([NH:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[CH2:13][CH:12]([NH:17][S:18]([CH:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])[CH2:11]3)[CH:5]=[CH:6][CH:7]=1)=[O:37])[CH3:34]

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 81531DiisopropylethylamineHCID 46899970N-[5-(3-aminophenyl)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide

Product 1

HCID 11538613N-[5-(3-{[(ethylamino)carbonyl]amino}phenyl)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamideYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Intermediate 4 (45 mg, 0.14 mmol), and diisopropylethylamine (36 mg, 0.28 mmol) in dry dichloromethane (3 ml) was cooled to 0° C. using an ice/methanol bath. Ethyl isocyanate (10 mg, 0.14 mmol) was added with stirring under argon and the whole mixture stirred at room temperature for 1 h. The reaction mixture was partitioned between dichloromethane (5 ml) and 1N hydrochloric acid (5 ml). The organic layer was removed and reduced to minimum volume under reduced pressure. The crude mixture was purified by flash column chromatography eluting from 0-50% ethyl acetate in 40-60° C. petroleum ether to give the title compound as a colourless oil (13 mg, 24%); mass spectrum (ES): Found 400 (ES−), C21H27N3O3S requires 401; 1H-NMR (400 MHz, CDCl3) δ 1.16 (3H, m), 1.38 (6H, m), 2.93 (2H, m), 3.19 (1H, m), 3.32 (4H, m), 4.32 (1H, m), 4.44 (1H, m), 4.82 (1H, m), 6.48 (1H, s), 7.23 (3H, m), 7.36 (3H, m), 7.54 (1H, m).

Workup

  1. stirringthe whole mixture stirred at room temperature for 1 h
  2. customThe reaction mixture was partitioned between dichloromethane (5 ml) and 1N hydrochloric acid (5 ml)
  3. customThe organic layer was removed
  4. customThe crude mixture was purified by flash column chromatography
  5. washeluting from 0-50% ethyl acetate in 40-60° C. petroleum ether

Sources & evidence

ORD record
ord-c22f17ca4c5d479a94b1bba71baea5c6
Source dataset
uspto-grants-2010_06
Patent number
US07741351B2

Reaction notes

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