Water → HCID 18442583, compound

HRID 458806Notes

Reaction equation

HRID 458806 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH2:5][C:6]1[C:7]2[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[CH:14][C:8]=2[NH:9][C:10](=[O:13])[CH2:11][N:12]=1.C([BH3-])#N.[Na+].O>C(O)(=O)C.CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH2:5][CH:6]1[NH:12][CH2:11][C:10](=[O:13])[NH:9][C:8]2[CH:14]=[C:15]([O:20][CH3:21])[C:16]([O:18][CH3:19])=[CH:17][C:7]1=2

Participants

6

Reactant 3

HCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 135772691HCID 135772691, compound

Product 1

HCID 18442583HCID 18442583, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5-(3,4-dichloro-benzyl)-7,8-dimethoxy-1,3-dihydro-benzo[e][1,4]diazepin-2-one (0.48 g, 1.17 mmol) in glacial acetic acid (1.67 ml) and methanol (9.4 ml) was stirred at 0° C. under nitrogen. Sodium cyanoborohydride (0.148 g, 2.23 mmol) was added portionwise and the reaction mixture was stirred at 0° C. for 30 min, and then at RT for 2 h. Water (17 ml) was added dropwise and the product was extracted with dichloromethane, washed with aqueous 1N ammonia. The organic phase was dried over magnesium sulfate, filtered and the solvent was removed under vacuum. The resulting yellow oil crystallized under HV (0.19 g, 41%).

Workup

  1. waitat RT for 2 h
  2. extractionthe product was extracted with dichloromethane
  3. washwashed with aqueous 1N ammonia
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed under vacuum
  7. customThe resulting yellow oil crystallized under HV (0.19 g, 41%)

Sources & evidence

ORD record
ord-bc00c1da1cd24543ad74ccd2dcc2e74d
Source dataset
uspto-grants-2007_03
Patent number
US07192950B2

Reaction notes

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