Hydrochloric Acid → HCID 136128349, compound

HRID 220921Notes

Reaction equation

HRID 220921 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][CH:34]([CH:37]=[O:38])[CH2:33][CH2:32]1)=[O:30].Cl>CO>[OH:38][CH2:37][CH:34]1[CH2:35][CH2:36][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])[CH2:32][CH2:33]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 136128376HCID 136128376, compound

Product 1

HCID 136128349HCID 136128349, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (12 mg, 0.32 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}-piperidine-4-carbaldehyde from Example E58.1 (74 mg, 0.15 mmol) in methanol (6 ml). The mixture was stirred for 1 h at room temperature, acidified with 1M HCl and concentrated in vacuo. The residue was dissolved in EtOAc, washed with saturated NaHCO3 then brine, dried and concentrated in vacuo. The residue was crystallised from chloroform and pet. ether to give a white powder identified as the title compound (28 mg, 38%).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with saturated NaHCO3
  4. dry with materialbrine, dried
  5. concentrationconcentrated in vacuo
  6. customThe residue was crystallised from chloroform and pet. ether
  7. customto give a white powder

Sources & evidence

ORD record
ord-ed8b071d082a43ab89314f01b331fd49
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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