Acetic Acid → HCID 57883545, compound

HRID 2384197Notes

Reaction equation

HRID 2384197 reaction equation
[CH:1]1([N:7]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[C:8]([NH:10][C:11]2[S:12][C:13]([CH:16]=O)=[CH:14][N:15]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(=O)C.[CH2:28]([O:30][C:31](=[O:40])[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([NH2:39])=[CH:35][CH:34]=1)[CH3:29].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH2:28]([O:30][C:31](=[O:40])[CH2:32][C:33]1[CH:34]=[CH:35][C:36]([NH:39][CH2:16][C:13]2[S:12][C:11]([NH:10][C:8]([N:7]([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]3)=[O:9])=[N:15][CH:14]=2)=[CH:37][CH:38]=1)[CH3:29]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 225219p-Aminophenylacetic acid ethyl esterHCID 5049666Sodium triacetoxyborohydrideHCID 578834711,1-Dicyclohexyl-3-(5-formyl-thiazol-2-yl)-urea

Product 1

HCID 57883545HCID 57883545, compoundYield 30%

Procedure

Prepared as described in general procedure (P) using 1,1-dicyclohexyl-3-(5-formyl-thiazol-2-yl)-urea (100 mg. 0.298 mmol), acetic acid (17 μL, 0.29 mmol), (4-amino-phenyl)-acetic acid ethyl ester (14 mg, 0.45 mmol) and sodium triacetoxyborohydride (101 mg, 0.48 mmol) to afford 43 mg (30%) of the desired product after purification.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-07f26ebfd92e4d31b92b58daadc4aa30
Source dataset
uspto-grants-2012_09
Patent number
US08263634B2

Reaction notes

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