Sodium triacetoxyborohydride → 1,1-Dicyclohexyl-3-[5-(1,1-dioxo-thiomorpholin-4-ylmethyl)-thiazol-2-yl]-urea

HRID 253847Notes

Reaction equation

HRID 253847 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.[O:25]=[S:26]1(=[O:32])[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]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]([NH:10][C:11]2[S:12][C:13]([CH2:16][N:29]3[CH2:30][CH2:31][S:26](=[O:32])(=[O:25])[CH2:27][CH2:28]3)=[CH:14][N:15]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 12324096Thiomorpholine 1,1-dioxide hydrochlorideHCID 578834711,1-Dicyclohexyl-3-(5-formyl-thiazol-2-yl)-urea

Product 1

HCID 578839361,1-Dicyclohexyl-3-[5-(1,1-dioxo-thiomorpholin-4-ylmethyl)-thiazol-2-yl]-ureaYield 18%

Procedure

Prepared as described in general procedure (P) using 1,1-dicyclohexyl-3-(5-formyl-thiazol-2-yl)-urea (67 mg. 0.20 mmol), 1,1-dioxo-thiomorpholine hydrochloride (52 mg, 0.30 mmol) and sodium triacetoxyborohydride (51 mg, 0.24 mmol) to afford 16 mg (18%) of the desired product after purification.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-f3c0b9efe8a347f2b563d383431ca11e
Source dataset
uspto-grants-2011_01
Patent number
US07872139B2

Reaction notes

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