Hydrazine → 2-Amino-ethanesulfonic acid {2-[3-(2-cyclopentanecarbonyl-4-methyl-phenyl)-ureido]-thiazol-4-ylmethyl}-amide

HRID 131869Notes

Reaction equation

HRID 131869 reaction equation
[NH2:1][CH2:2][C:3]1[N:4]=[C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=2[C:19]([CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:20])=[O:10])[S:6][CH:7]=1.O=C1C2C(=CC=CC=2)C(=O)[N:28]1[CH2:37][CH2:38][S:39](Cl)(=[O:41])=[O:40].NN>>[CH:21]1([C:19]([C:13]2[CH:14]=[C:15]([CH3:18])[CH:16]=[CH:17][C:12]=2[NH:11][C:9](=[O:10])[NH:8][C:5]2[S:6][CH:7]=[C:3]([CH2:2][NH:1][S:39]([CH2:38][CH2:37][NH2:28])(=[O:41])=[O:40])[N:4]=2)=[O:20])[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

4

Reactant 3

HCID 9321HydrazineHCID 3087392-Phthalimidoethanesulfonyl chlorideHCID 597328161-(4-Aminomethyl-thiazol-2-yl)-3-(2-cyclopentanecarbonyl-4-methylphenyl)-urea

Product 1

HCID 597327422-Amino-ethanesulfonic acid {2-[3-(2-cyclopentanecarbonyl-4-methyl-phenyl)-ureido]-thiazol-4-ylmethyl}-amideYield 89.3%

Procedure

2-Amino-ethanesulfonic acid {2-[3-(2-cyclopentanecarbonyl-4-methyl-phenyl)-ureido]-thiazol-4-ylmethyl}-amide (104 mg, 83%) was prepared from 1-(4-aminomethyl-thiazol-2-yl)-3-(2-cyclopentanecarbonyl-4-methyl-phenyl)-urea (90 mg, 0.25 mmol) and 2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-ethanesulfonyl chloride (70 mg, 0.25 mmol) following the general procedure T. This intermediate was deprotected by heating with excess of hydrazine (0.2 mL, 1.0 M. in THF).

Sources & evidence

ORD record
ord-bf811f6af8b54d16b2ce1e9ebaf5d8b0
Source dataset
uspto-grants-2008_06
Patent number
US07384967B2

Reaction notes

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