Hydrochloric Acid → HCID 24750645, compound

HRID 252278Notes

Reaction equation

HRID 252278 reaction equation
[Br:1][C:2]1[S:6][C:5]([NH:7][C:8](=[O:20])[NH:9][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=2)(=[O:12])=[O:11])=[N:4][C:3]=1[C:21](OCC)=[O:22].[BH4-].[Na+].Cl>O1CCCC1>[Br:1][C:2]1[S:6][C:5]([NH:7][C:8]([NH:9][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=2)(=[O:12])=[O:11])=[O:20])=[N:4][C:3]=1[CH2:21][OH:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 24752792HCID 24752792, compound

Product 1

HCID 24750645HCID 24750645, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 5-bromo-2-({[(3-methylphenyl)sulfonyl]carbamoyl}amino)-1,3-thiazole-4-carboxylate (50 mg, 0.11 mmol) was treated with sodium borohydride (21 mg, 0.56 mmol) in tetrahydrofuran (2 ml) for 2 days at room temp. 0.5 M HCl was added and the quenched reaction mixture was purified on preparative HPLC yielding 21 mg of the title compound as an amorphous solid. MS (ES): m/e 404.1 (M−H)

Workup

  1. customthe quenched reaction mixture
  2. customwas purified on preparative HPLC

Sources & evidence

ORD record
ord-9107377fe4b34fee9e7c586dd4eabcb3
Source dataset
uspto-grants-2011_01
Patent number
US07868030B2

Reaction notes

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