Sodium triacetoxyborohydride → 4-[3-{5-[4-(2-Methoxycarbonyl-acetyl)-piperazin-1-ylmethyl]-thiazol-2-yl}-1-(4-methyl cyclohexyl)-ureido]-piperidine-1-carboxylic acid tert-butyl ester

HRID 531999Notes

Reaction equation

HRID 531999 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH:25]2[CH2:30][CH2:29][CH:28]([CH3:31])[CH2:27][CH2:26]2)[C:15]([NH:17][C:18]2[S:19][C:20]([CH:23]=O)=[CH:21][N:22]=2)=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:33][O:34][C:35](=[O:45])[CH2:36][C:37](=[O:44])[N:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH:25]2[CH2:30][CH2:29][CH:28]([CH3:31])[CH2:27][CH2:26]2)[C:15]([NH:17][C:18]2[S:19][C:20]([CH2:23][N:41]3[CH2:40][CH2:39][N:38]([C:37](=[O:44])[CH2:36][C:35]([O:34][CH3:33])=[O:45])[CH2:43][CH2:42]3)=[CH:21][N:22]=2)=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 578838034-[3-(5-Formyl-thiazol-2-yl)-1-(4-methyl-cyclohexyl)-ureido]-piperidine-1-carboxylic acid tert-butyl esterHCID 668720843-Oxo-3-piperazin-1-yl-propionic acid methyl ester hydrochloride

Product 1

HCID 578836444-[3-{5-[4-(2-Methoxycarbonyl-acetyl)-piperazin-1-ylmethyl]-thiazol-2-yl}-1-(4-methyl cyclohexyl)-ureido]-piperidine-1-carboxylic acid tert-butyl esterYield 25%

Procedure

Prepared as described in general procedure (P) using 4-[3-(5-formyl-thiazol-2-yl)-1-(4-methyl-cyclohexyl)-ureido]-piperidine-1-carboxylic acid tert-butyl ester (68 mg, 0.15 mmol), 3-oxo-3-piperazin-1-yl-propionic acid methyl ester hydrochloride (54 mg, 0.19 mmol) and sodium triacetoxy-borohydride (38 mg, 0.18 mmol) to afford 23 mg (25%) of the desired product after purification.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-f79b7faa9be94abe8fc30ce7ca847e0b
Source dataset
uspto-grants-2014_10
Patent number
USRE045183E1

Reaction notes

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