2-Methylbutanal → HCID 24863075, compound

HRID 1353525Notes

Reaction equation

HRID 1353525 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][CH:11]([NH:20][C:21]([N:23]3[CH2:28][CH2:27][CH:26]([N:29]4[CH2:38][C:37]5[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=5)[NH:31][C:30]4=[O:39])[CH2:25][CH2:24]3)=[O:22])[C:12](=[O:19])[N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[CH3:40][CH:41]([CH2:44][CH3:45])[CH:42]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][CH:11]([NH:20][C:21]([N:23]3[CH2:24][CH2:25][CH:26]([N:29]4[CH2:38][C:37]5[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=5)[NH:31][C:30]4=[O:39])[CH2:27][CH2:28]3)=[O:22])[C:12]([N:13]3[CH2:18][CH2:17][N:16]([CH2:40][CH:41]([CH3:42])[CH2:44][CH3:45])[CH2:15][CH2:14]3)=[O:19])=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 72842-MethylbutanalHCID 5049666Sodium triacetoxyborohydrideHCID 24863074HCID 24863074, compound

Product 1

HCID 24863075HCID 24863075, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of 4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidine-1-carboxylic acid [1-(1H-indazol-5-ylmethyl)-2-oxo-2-piperazin-1-yl-ethyl]-amide (100 mg, 0.188 mmol) in methanol (25 mL) was treated with 2-methyl-butyraldehyde (0.03 ml, 0.376 mmol). After 1 h at room temperature, sodium triacetoxyborohydride (80 mg, 0.316 mmol) was added. The mixture was allowed to stir overnight. The solution was filtered through an SCX cartridge. The cartridge was eluted first with methanol and then with a 1M solution of ammonia in methanol. The solvent was removed in vacuo to give the desired product in 50% yield. LC/MS: tR=1.31 min, 601(MH)+.

Workup

  1. filtrationThe solution was filtered through an SCX cartridge
  2. washThe cartridge was eluted first with methanol
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-c95527c44e814d9dbe7886910ea4db80
Source dataset
uspto-grants-2007_05
Patent number
US07220862B2

Reaction notes

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