Sodium borohydride → HCID 178489063, compound

HRID 2174110Notes

Reaction equation

HRID 2174110 reaction equation
[C:1]([C:3]1[CH:29]=[CH:28][C:6]2[NH:7][C:8]([CH:10]([C:16]3[C:24]([O:25][CH3:26])=[CH:23][C:22]([CH3:27])=[C:21]4[C:17]=3[CH:18]=[CH:19][NH:20]4)[CH2:11][C:12](OC)=[O:13])=[N:9][C:5]=2[CH:4]=1)#[N:2].[BH4-].[Na+]>CO>[OH:13][CH2:12][CH2:11][CH:10]([C:8]1[NH:7][C:6]2[CH:28]=[CH:29][C:3]([C:1]#[N:2])=[CH:4][C:5]=2[N:9]=1)[C:16]1[C:24]([O:25][CH3:26])=[CH:23][C:22]([CH3:27])=[C:21]2[C:17]=1[CH:18]=[CH:19][NH:20]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178500072HCID 178500072, compound

Product 1

HCID 178489063HCID 178489063, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (±)-methyl 3-(5-cyano-1H-benzo[d]imidazol-2-yl)-3-(5-methoxy-7-methyl-1H-indol-4-yl)propanoate (Example 145-C) (50 mg, 0.129 mmol) in MeOH (1.3 mL) was added NaBH4 (121 mg, 3.25 mmol) at 0° C. The reaction mixture was allowed to reach rt and stirred for 48 hrs. The reaction mixture was quenched with water at 0° C. and extracted with EtOAc (2×). The combined organic layers were passed through a phase separator and concentrated and absorbed onto silica to purify via FCC with DCM/MeOH (100/0 to 95/5) to obtain the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.04-12.30 (m, 1H) 10.89 (br. s., 1H) 8.10 (s, 1H) 7.68-7.77 (m, 1H) 7.38-7.51 (m, 1H) 6.99-7.21 (m, 1H) 6.78 (s, 1H) 6.10 (br. s., 1H) 4.99 (t, J=7.33 Hz, 1H) 4.36-4.57 (m, 1H) 3.74 (s, 3H) 3.42 (td, J=11.56, 5.68 Hz, 2H) 2.77 (dd, J=13.39, 6.82 Hz, 1H) 2.44 (s, 3H) 2.11-2.23 (m, 1H). HRMS calcd. for C21H20N4O2 (M+H)+ 361.1651. found 361.1659.

Workup

  1. customto reach rt
  2. customThe reaction mixture was quenched with water at 0° C.
  3. extractionextracted with EtOAc (2×)
  4. concentrationconcentrated
  5. customabsorbed onto silica
  6. customto purify via FCC with DCM/MeOH (100/0 to 95/5)

Sources & evidence

ORD record
ord-6f1a3eb60c5c4cd6b6d6ce67163cb171
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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