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Sodium borohydride → HCID 178489249, compound

HRID 1012936
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Reaction equation

HRID 1012936 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([O:12][C@H:13]3[CH2:18][CH2:17][C@H:16]([NH2:19])[CH2:15][CH2:14]3)[S:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.[O:20]=[C:21]1[NH:26][C:25]2[CH:27]=[C:28]([CH:31]=O)[CH:29]=[CH:30][C:24]=2[O:23][CH2:22]1.[BH4-].[Na+]>ClCCCl.CO>[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([O:12][C@H:13]3[CH2:18][CH2:17][C@H:16]([NH:19][CH2:31][C:28]4[CH:29]=[CH:30][C:24]5[O:23][CH2:22][C:21](=[O:20])[NH:26][C:25]=5[CH:27]=4)[CH2:15][CH2:14]3)[S:11][C:7]=2[CH:6]=[CH:5][CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 107736383-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbaldehydeHCID 178489248HCID 178489248, compound2×

Product 1

HCID 178489249HCID 178489249, compoundYield 16.4%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent
HCID 887
Methanol
Solvent

Procedure

trans-4-(4-methoxy-benzothiazol-2-yloxy)-cyclohexylamine (0.5 mmol, intermediate 25.b) and 3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbaldehyde (0.5 mmol) were dissolved in DCE (4 ml) and MeOH (4 ml). The mixture was stirred at RT overnight, NaBH4 (1 eq) was added and stirring continued for 1 h. The reaction mixture was partitioned between DCM and NH4OH. The organic layer was dried over MgSO4 and concentrated under reduced pressure. Purification by chromatography (EtOAc/MeOH 9:1 +1% NH4OH) and crystallisation from ether gave 36 mg (16%) of the title compound as a colourless solid.

Workup

  1. stirringstirring
  2. waitcontinued for 1 h
  3. customThe reaction mixture was partitioned between DCM and NH4OH
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customPurification
  7. customby chromatography (EtOAc/MeOH 9:1 +1% NH4OH) and crystallisation from ether

Sources & evidence

ORD record
ord-f535ae210fb44ff6bbc5d3b351e7c30b
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07981886B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes