Methanol → HCID 18548762, compound

HRID 1266850Notes

Reaction equation

HRID 1266850 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]3[CH2:17][C:18](=[O:32])[NH:19][C:20]4[CH:26]=[C:25]([N:27]5[CH:31]=[CH:30][CH:29]=[CH:28]5)[CH:24]=[CH:23][C:21]=4[N:22]=3)[CH:11]=2)[O:8][CH:9]=1)=O.CO.[BH4-].[Li+]>C1COCC1>[OH:2][CH2:3][C:5]1[N:6]=[C:7]([C:10]2[CH:11]=[C:12]([C:16]3[CH2:17][C:18](=[O:32])[NH:19][C:20]4[CH:26]=[C:25]([N:27]5[CH:28]=[CH:29][CH:30]=[CH:31]5)[CH:24]=[CH:23][C:21]=4[N:22]=3)[CH:13]=[CH:14][CH:15]=2)[O:8][CH:9]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 69779806HCID 69779806, compound

Product 1

HCID 18548762HCID 18548762, compoundYield 30.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 2-[3-(4-oxo-7-pyrrol-1-yl-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)-phenyl]-oxazole-4-carboxylic acid methyl ester (Example 25) (88 mg, 0.2 mmol) in THF (1.5 mL) were added successively MeOH (0.012 mL) and lithium borohydride (6.5 mg, 0.3 mmol). The mixture was stirred at 40° C. for 1 h and then partitioned between EtOAc and 1N HCl. The organic layer was washed with brine, dried and evaporated in vacuum. The residue was chromatographed on silica gel using EtOAc/hexane (1:2) as eluents to give the title compound (24 mg) as light-yellow solid.

Workup

  1. custompartitioned between EtOAc and 1N HCl
  2. washThe organic layer was washed with brine
  3. customdried
  4. customevaporated in vacuum
  5. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-84010bc3de7d4c9287fa0b1dfa9ecb6a
Source dataset
uspto-grants-2003_04
Patent number
US06548495B2

Reaction notes

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