Sodium borohydride → HCID 178489057, compound

HRID 2174125Notes

Reaction equation

HRID 2174125 reaction equation
[C:1]([C:3]1[CH:31]=[CH:30][C:6]2[NH:7][C:8]([CH:10]([C:18]3[C:26]([O:27][CH3:28])=[CH:25][C:24]([CH3:29])=[C:23]4[C:19]=3[CH:20]=[CH:21][NH:22]4)[CH2:11][CH:12]([CH3:17])[C:13](OC)=[O:14])=[N:9][C:5]=2[CH:4]=1)#[N:2].[BH4-].[Na+]>CO>[OH:14][CH2:13][CH:12]([CH3:17])[CH2:11][CH:10]([C:8]1[NH:7][C:6]2[CH:30]=[CH:31][C:3]([C:1]#[N:2])=[CH:4][C:5]=2[N:9]=1)[C:18]1[C:26]([O:27][CH3:28])=[CH:25][C:24]([CH3:29])=[C:23]2[C:19]=1[CH:20]=[CH:21][NH:22]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178500185HCID 178500185, compound

Product 1

HCID 178489057HCID 178489057, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of (±)-methyl 4-(5-cyano-1H-benzo[d]imidazol-2-yl)-4-(5-methoxy-7-methyl-1H-indol-4-yl)-2-methylbutanoate (Example 151-B) (95 mg, 0.228 mmol) in MeOH (3 mL) was treated with sodium borohydride (220 mg, 6.7 mmol) and heated at 60° C. for 4 hours. The reaction was cooled to room temperature and quenched with a saturated solution of ammonium chloride. The product was extracted with ethyl acetate, the organics were dried over sodium sulfate, concentrated and purified via reversed phase FCC(C18 gold column, 10-70% ACN:water) to obtain the title compound as a mixture of diastereomes. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.89 (br. s., 1H) 7.96 (br. s., 1H) 7.55 (br. s., 1H) 7.46-7.52 (m, 1H) 7.15 (t, J=2.75 Hz, 1H) 6.79 (s, 1H) 6.14 (d, J=1.96 Hz, 1H) 5.01 (dd, J=10.39, 4.89 Hz, 1H) 3.70-3.81 (m, 3H) 3.17-3.23 (m, 1H) 3.09-3.16 (m, 1H) 2.45 (d, J=0.61 Hz, 3H) 2.38 (ddd, J=13.57, 10.39, 3.67 Hz, 1H) 2.14-2.24 (m, 1H) 1.21-1.33 (m, 2H) 0.95 (d, J=6.60 Hz, 3H). HRMS calcd. for C23H24N4O2 (M+H)+ 389.1975. found 389.1978.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customquenched with a saturated solution of ammonium chloride
  3. extractionThe product was extracted with ethyl acetate
  4. dry with materialthe organics were dried over sodium sulfate
  5. concentrationconcentrated
  6. custompurified via reversed phase FCC(C18 gold column, 10-70% ACN

Sources & evidence

ORD record
ord-0488e40d907d4af6b7a17c45bba5a5e7
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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