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Sodium borohydride → 4-(6-Chloro-benzo[b]thiophene-2-sulfonyl)-1-(4-hydroxy-4,5,6,7-tetrahydro-benzothiazol-2-ylmethyl)-piperazin-2-one

HRID 1433074
Notes
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Reaction equation

HRID 1433074 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([S:10]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][C:20]4[S:21][C:22]5[CH2:28][CH2:27][CH2:26][C:25](=[O:29])[C:23]=5[N:24]=4)[C:15](=[O:30])[CH2:14]3)(=[O:12])=[O:11])[S:7][C:6]=2[CH:31]=1.[BH4-].[Na+]>CCO.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([S:10]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][C:20]4[S:21][C:22]5[CH2:28][CH2:27][CH2:26][CH:25]([OH:29])[C:23]=5[N:24]=4)[C:15](=[O:30])[CH2:14]3)(=[O:11])=[O:12])[S:7][C:6]=2[CH:31]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 670150242-[4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-6,7-dihydro-5H-benzothiazol-4-one

Product 1

HCID 670141644-(6-Chloro-benzo[b]thiophene-2-sulfonyl)-1-(4-hydroxy-4,5,6,7-tetrahydro-benzothiazol-2-ylmethyl)-piperazin-2-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent
HCID 8857
Ethyl Acetate
Solvent

Procedure

To the suspension of 2-[4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-6,7-dihydro-5H-benzothiazol-4-one (7 mg, 0.01 mmol) in EtOH (1 mL) is added sodium borohydride (3 mg, 0.08 mmol). After 15 min the reaction is diluted with EtOAc and washed with 1N HCl, NaHCO3 and brine. The solution is dried (MgSO4) and concentrated to provide 4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-1-(4-hydroxy-4,5,6,7-tetrahydro-benzothiazol-2-ylmethyl)-piperazin-2-one. 1H NMR (300 MHz, CDCl3) δ 7.88-7.82 (m, 3H), 7.46 (dd, 1H), 4.83-4.81 (m, 1H), 4.76 (s, 1H), 4.75 (s, 1H), 3.92 (s, 1H), 3.91 (s, 1H), 3.62-3.55 (m, 2H), 3.47-3.41 (m, 2H), 2.76-2.62 (m, 2H), 2.05-1.78 (m, 4H); MS (Ion Spray) 498 (M+H)+.

Workup

  1. washwashed with 1N HCl, NaHCO3 and brine
  2. dry with materialThe solution is dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b5c2e99e0ac540878d4ddc44bd83d7e7
Source dataset
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07612075B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes