3,3-Dimethylbutanal → HCID 136128417, compound

HRID 220946Notes

Reaction equation

HRID 220946 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[CH2:3][CH:4]=O.[CH3:8][C:9]1[CH:25]=[C:24]([C:26]([N:28]2[CH2:37][C:36]3[CH:35]=[N:34][N:33]([CH3:38])[C:32]=3[NH:31][C:30]3[CH:39]=[CH:40][CH:41]=[CH:42][C:29]2=3)=[O:27])[CH:23]=[CH:22][C:10]=1[CH2:11][NH:12][C:13](=[O:21])[CH2:14][CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[CH3:1][C:2]([CH3:7])([CH3:6])[CH2:3][CH2:4][N:18]1[CH2:17][CH2:16][CH:15]([CH2:14][C:13]([NH:12][CH2:11][C:10]2[CH:22]=[CH:23][C:24]([C:26]([N:28]3[CH2:37][C:36]4[CH:35]=[N:34][N:33]([CH3:38])[C:32]=4[NH:31][C:30]4[CH:39]=[CH:40][CH:41]=[CH:42][C:29]3=4)=[O:27])=[CH:25][C:9]=2[CH3:8])=[O:21])[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 763353,3-DimethylbutanalHCID 5003444Sodium cyanoborohydrideHCID 136128368HCID 136128368, compound

Product 1

HCID 136128417HCID 136128417, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 10129899Acetic acid methanolSolvent

Procedure

3,3-Dimethylbutyraldehyde (0.048 ml, 0.38 mmol) was added to a solution of N-[2-methyl-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-benzyl]-2-piperidin-4-yl-acetamide from Example E91 (130 mg, 0.25 mmol) in methanol/acetic acid (49:1, v/v, 2.5 ml) and the mixture was stirred at room temperature for 1 h. Sodium cyanoborohydride (24 mg, 0.38 mmol) was added, and the mixture was stirred at room temperature for 18 h then concentrated in vacuo. The residue was dissolved in dichloromethane, washed with saturated Na—HCO3 then brine, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel through an isolute (eluant; 1.5% 35% ammonia:15% methanol:83.5% dichloromethane) to give a white solid identified as the title compound (107 mg, 75%).

Workup

  1. stirringthe mixture was stirred at room temperature for 18 h
  2. concentrationthen concentrated in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with saturated Na—HCO3
  5. dry with materialbrine, dried
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel through an isolute (eluant; 1.5% 35% ammonia:15% methanol:83.5% dichloromethane)
  8. customto give a white solid

Sources & evidence

ORD record
ord-aa27074589ec4b69af634c12bb2414d5
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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