Water → HCID 70978277, compound

HRID 2281064Notes

Reaction equation

HRID 2281064 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([C:16]4[CH:21]=[CH:20][C:19]([CH2:22][N:23]5[CH2:27][C:26](=[O:28])[N:25]([CH3:29])[C:24]5=[O:30])=[CH:18][CH:17]=4)=[C:13]([CH:14]=[O:15])[C:8]=3[N:7]=[N:6]2)[CH2:3][CH2:2]1.[BH4-].[Na+].O>CO.ClCCl>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([C:16]4[CH:21]=[CH:20][C:19]([CH2:22][N:23]5[CH2:27][C:26](=[O:28])[N:25]([CH3:29])[C:24]5=[O:30])=[CH:18][CH:17]=4)=[C:13]([CH2:14][OH:15])[C:8]=3[N:7]=[N:6]2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 71468391HCID 71468391, compound

Product 1

HCID 70978277HCID 70978277, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(cyclopropylmethyl)-5-{4-[(3-methyl-2,4-dioxoimidazolidin-1-yl)methyl]phenyl}-1H-benzotriazole-4-carbaldehyde (Example 20, 72 mg, 0.18 mmol) in methanol (1.8 mL) was added sodium borohydride (6.8 mg, 0.18 mmol). After 1.5 hours, the mixture was treated with water, diluted with dichloromethane and washed with brine. The organic extract was dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified via silica gel chromatography (ethyl acetate/hexane gradient), providing the titled compound: 1H NMR (400 MHz, CDCl3) 7.54 (d, 1H, J=8.8 Hz), 7.42-7.45 (m, 3H), 7.35 (d, 2H, J=8.0 Hz), 5.12 (d, 2H, J=6.4 Hz), 4.65 (s, 2H), 4.55 (d, 2H, J=7.2 Hz), 3.83 (s, 2H), 3.08 (s, 3H), 1.40-1.47 (m, 1H), 0.67-0.71 (m, 2H), 0.51-0.55 (m, 2H) ppm. LRMS m/z (M+H) 406.0 found, 406.2 required.

Workup

  1. washwashed with brine
  2. extractionThe organic extract
  3. dry with materialwas dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified via silica gel chromatography (ethyl acetate/hexane gradient)

Sources & evidence

ORD record
ord-ff8eeba0b24d428c88ed5475cac649dd
Source dataset
uspto-grants-2015_09
Patent number
US09139576B2

Reaction notes

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