Dimethylformamide → HCID 71622058, compound

HRID 871027Notes

Reaction equation

HRID 871027 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([N:7]=[C:8]=[O:9])=[CH:3][CH:2]=1.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:22]([C:23]([NH2:25])=[O:24])=[C:21]([NH:26][C:27]([NH:29][CH2:30][CH2:31][CH2:32][N:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)=[O:28])[S:20][N:19]=2)=[CH:14][CH:13]=1.C(N(C(C)C)CC)(C)C.CN(C)C=O>O1CCCC1>[CH3:10][C:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:22]([C:23]([NH2:25])=[O:24])=[C:21]([NH:26][C:27]([NH:29][CH2:30][CH2:31][CH2:32][N:33]4[CH2:37][CH2:36][CH2:35][CH2:34]4)=[O:28])[S:20][N:19]=3)=[CH:14][CH:13]=2)=[O:9])=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 693254-Methylphenyl isocyanateHCID 81531DiisopropylethylamineHCID 71621929HCID 71621929, compound

Product 1

HCID 71622058HCID 71622058, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Para-Tolyl isocyanate (4.5 g 0.0339 mol) was added to a solution of 3-(4-aminophenyl)-5-({[(3-pyrrolidin-1-ylpropyl)amino]carbonyl}amino)isothiazole-4-carboxamide (12.0 g, 0.0308 mol), diisopropylethylamine (6.0 g, 0.046 mol) in mixture of tetrahydrofuran (300 mL) and dimethylformamide (50 ml) at ambient temperature over 20 min. The resulting mixture was stirred at ambient temperature for 2 hr. The reaction mixture was concentrated in vacuo to give off white solid, which was stirred in 20% tetrahydrofuran and ethyl acetate (200 mL) mixture, filtered the solid and washed with ethyl acetate the title compound as a white solid (15.8 g, 98%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto give off white solid, which
  3. filtrationethyl acetate (200 mL) mixture, filtered the solid
  4. washwashed with ethyl acetate the title compound as a white solid (15.8 g, 98%)

Sources & evidence

ORD record
ord-c5da25c2b642423388b676c8aec0d725
Source dataset
uspto-grants-2015_03
Patent number
US08969583B2

Reaction notes

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