Benzaldehyde → HCID 9893125, compound

HRID 2303278Notes

Reaction equation

HRID 2303278 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]([C:21]1[CH:26]=[C:25]([CH3:27])[N:24]=[C:23]([N:28]2[CH:32]=[CH:31][N:30]=[CH:29]2)[N:22]=1)[CH2:6][C:7]([NH:9][CH2:10][CH2:11][C:12]1[CH:20]=[CH:19][C:15]2[O:16][CH2:17][O:18][C:14]=2[CH:13]=1)=[O:8].[CH:33](=O)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.N1C=CC=CC=1.B>CO>[C:34]1([CH2:33][NH:1][CH2:2][CH2:3][CH2:4][N:5]([C:21]2[CH:26]=[C:25]([CH3:27])[N:24]=[C:23]([N:28]3[CH:32]=[CH:31][N:30]=[CH:29]3)[N:22]=2)[CH2:6][C:7]([NH:9][CH2:10][CH2:11][C:12]2[CH:20]=[CH:19][C:15]3[O:16][CH2:17][O:18][C:14]=3[CH:13]=2)=[O:8])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 2723995Borane;pyridineHCID 99109492-[(3-aminopropyl)[2-(1H-imidazol-1-yl)-6-methyl-4-pyrimidinyl]amino]-N-[2-(1,3-benzodioxol-5-yl)ethyl]acetamide

Product 1

HCID 9893125HCID 9893125, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 2-[(3-aminopropyl)[2-(1H-imidazol-1-yl)-6-methyl-4-pyrimidinyl]amino]-N-[2-(1,3-benzodioxol-5-yl)ethyl]acetamide (50 mg, 0.11 mmol) (a compound of formula (Yc6)) in methanol (2 mL) was added benzaldehyde (0.2 M in methanol, 68 μL, 0.14 mmol). After stirring for 15 minutes, borane-pyridine complex (0.2 M in methanol, 0.14 mmol) was added. After 2 hours, the solution was evaporated. The residue was partitioned into water and ethyl acetate. The aqueous layer was extracted twice with ethyl acetate. The combined ethyl acetate fractions were washed with brine, dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel (2:1 ethyl acetate/hexanes) to provide 2-[[3-(phenylmethylamino)propyl][2-(1H-imidazol-1-yl)-6-methyl-4-pyrimidinyl]amino]-N-[2-(1,3-benzodioxol-5-yl)ethyl]acetamide, a compound of formula (Yc8); as a white solid; NMR (CDCl3) 8.65 (s, 1), 7.7 (s, 1), 7.2 (br, 5), 7.1 (s, 1), 6.6 (d, 1), 6.55 (s, 1), 6.5 (d, 1), 6.1 (br, 2), 5.9 (s, 2), 3.95 (br, 2), 3.5 (br, 6), 2.7 (m, 3), 2.35 (s, 6) ppm.

Workup

  1. waitAfter 2 hours
  2. customthe solution was evaporated
  3. customThe residue was partitioned into water and ethyl acetate
  4. extractionThe aqueous layer was extracted twice with ethyl acetate
  5. washThe combined ethyl acetate fractions were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on silica gel (2:1 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-b0c99168df20419c993f110562dd264b
Source dataset
uspto-grants-2002_08
Patent number
US06432947B1

Reaction notes

Loading…