Sodium triacetoxyborohydride → Propane-2-sulfonic acid {1-[2-(3,3-dicyclohexyl-ureido)-thiazol-5-ylmethyl]-piperidin-4-yl}-amide

HRID 531986Notes

Reaction equation

HRID 531986 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.Cl.[NH:25]1[CH2:30][CH2:29][CH:28]([NH:31][S:32]([CH:35]([CH3:37])[CH3:36])(=[O:34])=[O:33])[CH2:27][CH2:26]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH:1]1([N:7]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[C:8](=[O:9])[NH:10][C:11]2[S:12][C:13]([CH2:16][N:25]3[CH2:26][CH2:27][CH:28]([NH:31][S:32]([CH:35]([CH3:37])[CH3:36])(=[O:33])=[O:34])[CH2:29][CH2:30]3)=[CH:14][N:15]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 53255852N-(Piperidin-4-yl)propane-2-sulfonamidehydrochlorideHCID 578834711,1-Dicyclohexyl-3-(5-formyl-thiazol-2-yl)-urea

Product 1

HCID 57883480Propane-2-sulfonic acid {1-[2-(3,3-dicyclohexyl-ureido)-thiazol-5-ylmethyl]-piperidin-4-yl}-amideYield 11%

Procedure

Prepared as described in general procedure (P) using 1,1-dicyclohexyl-3-(5-formyl-thiazol-2-yl)-urea (21 mg, 0.07 mmol), propane-2-sulfonic acid piperidin-4-yl amide hydrochloride (17 mg, 0.077 mmol) and sodium triacetoxyborohydride (19 mg, 0.09 mmol) to afford 4 mg (11%) of the desired product after purification.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-30a36583653a4ef08cf089cd6b24309a
Source dataset
uspto-grants-2014_10
Patent number
USRE045183E1

Reaction notes

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