Sodium borohydride → HCID 136128392, compound

HRID 220930Notes

Reaction equation

HRID 220930 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[CH:9]=[C:8]([C:10]([N:12]2[CH2:21][C:20]3[CH:19]=[N:18][N:17]([CH3:22])[C:16]=3[NH:15][C:14]3[CH:23]=[CH:24][CH:25]=[CH:26][C:13]2=3)=[O:11])[CH:7]=[CH:6][C:5]=1[CH2:27][CH2:28][C:29]([N:31]1[CH2:36][CH2:35][C:34](=[O:37])[CH2:33][CH2:32]1)=[O:30]>CO.C(O)(=O)C>[OH:37][CH:34]1[CH2:33][CH2:32][N:31]([C:29](=[O:30])[CH2:28][CH2:27][C:5]2[CH:6]=[CH:7][C:8]([C:10]([N:12]3[CH2:21][C:20]4[CH:19]=[N:18][N:17]([CH3:22])[C:16]=4[NH:15][C:14]4[CH:23]=[CH:24][CH:25]=[CH:26][C:13]3=4)=[O:11])=[CH:9][C:4]=2[CH3:3])[CH2:36][CH2:35]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 136128357HCID 136128357, compound

Product 1

HCID 136128392HCID 136128392, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 10129899Acetic acid methanolSolvent

Procedure

Sodium borohydride (4 mg, 0.1 mmol) was added to a solution of 1-{3-[2-methyl-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-phenyl]-propionyl}-piperidin-4-one (Compound number 701) (50 mg, 0.11 mmol) in methanol/acetic acid (99:1, v/v, 100 ml) and the mixture was stirred at room temperature for 1 h. Sodium borohydride (4 mg, 0.11 mmol) was added again and the mixture was stirred for 1 h at room temperature then concentrated in vacuo. The residue was dissolved in di-chloromethane, washed with saturated NaHCO3 then brine, dried and concentrated in vacuo to give a white powder identified as the title compound (28 mg, 56%).

Workup

  1. stirringthe mixture was stirred for 1 h at room temperature
  2. concentrationthen concentrated in vacuo
  3. dissolutionThe residue was dissolved in di-chloromethane
  4. washwashed with saturated NaHCO3
  5. dry with materialbrine, dried
  6. concentrationconcentrated in vacuo
  7. customto give a white powder

Sources & evidence

ORD record
ord-47474e3d5fb9485dad8175996a9029b9
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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