Sodium borohydride → HCID 54670337, compound

HRID 1404778Notes

Reaction equation

HRID 1404778 reaction equation
[BH4-].[Na+].[N:3]1[C:12]2[C:7](=[CH:8][C:9]([CH2:13][N:14]3[C:18]4=[N:19][C:20]([C:23]5[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=5)[CH:26]=[O:27])=[CH:21][CH:22]=[C:17]4[N:16]=[N:15]3)=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1>CO>[N:3]1[C:12]2[C:7](=[CH:8][C:9]([CH2:13][N:14]3[C:18]4=[N:19][C:20]([C:23]5[CH:24]=[C:25]([CH2:26][OH:27])[CH:28]=[CH:29][CH:30]=5)=[CH:21][CH:22]=[C:17]4[N:16]=[N:15]3)=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 54670419HCID 54670419, compound

Product 1

HCID 54670337HCID 54670337, compoundYield 24.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (0.018 g, 0.493 mmol) was added to a solution of example 3 (0.180 g, 0.493 mmol) in methanol (4 ml), cooled to 0° C., and stirred 1 h. Ice-cold water was added to the mixture, extracted with ethyl acetate, washed with brine, dried over sodium sulphate and concentrated. The crude product was purified by column chromatography with methanol: dichloromethane to afford the title compound as a yellow solid (0.044 g, 24%). M.P. 191-193° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 8.88 (dd. J=4.2, 1.7 Hz, 1H), 8.63 (d, J=8.7 Hz, 1H), 8.38 (d, J=8.3 Hz, 1H), 8.21 (d, J=8.3 Hz, 2H), 8.12 (d, J=8.8 Hz, 1H), 8.02 (s, 1H), 8.02 (d, J=8.8 Hz, 1H), 7.83 (dd, J=8.7, 2.0 Hz, 1H), 7.53 (m, 3H), 6.20 (s, 2H), 5.30 (t, J=5.7 Hz, 1H), 4.58 (d, J=5.4 Hz, 2H). MS (m/z): 368.37 (M30+1).

Workup

  1. additionIce-cold water was added to the mixture
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography with methanol

Sources & evidence

ORD record
ord-0b05788881e044d4a18867b9939b8c51
Source dataset
uspto-grants-2014_12
Patent number
US08912331B2

Reaction notes

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