Acetone → HCID 66832572, compound

HRID 2044073Notes

Reaction equation

HRID 2044073 reaction equation
[C:1]([NH:9][C@@H:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16]2[CH:24]=[CH:23][C:19]([C:20]([NH2:22])=[O:21])=[C:18]([NH:25][C:26]3[CH:31]=[CH:30][C:29]([N:32]4[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]4)=[CH:28][CH:27]=3)[N:17]=2)[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:38][C:39](=O)[CH3:40].C([BH3-])#N.[Na+]>CO>[C:1]([NH:9][C@@H:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16]2[CH:24]=[CH:23][C:19]([C:20]([NH2:22])=[O:21])=[C:18]([NH:25][C:26]3[CH:27]=[CH:28][C:29]([N:32]4[CH2:33][CH2:34][N:35]([CH:39]([CH3:40])[CH3:38])[CH2:36][CH2:37]4)=[CH:30][CH:31]=3)[N:17]=2)[CH2:11]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 5003444Sodium cyanoborohydrideHCID 66832619HCID 66832619, compound

Product 1

HCID 66832572HCID 66832572, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of (R)-6-(3-benzamidopiperidin-1-yl)-2-(4-(piperazin-1-yl)phenylamino)nicotinamide (50 mg, 0.100 mmol) and propan-2-one (58.1 mg, 1.001 mmol) in MeOH (1 mL) was added sodium cyanoborohydride (12.58 mg, 0.200 mmol). The reaction mixture was quenched with satd. NaHCO3, extracted twice with CH2Cl2, and concentrated. The residue was purified by prep-HPLC. The product containing fractions were collected, basified with 1N NaOH, extracted with CH2Cl2, and concentrated to give 30 mg of (R)-6-(3-benzamidopiperidin-1-yl)-2-(4-(4-isopropylpiperazin-1-yl)phenylamino)nicotinamide as yellow solid. LCMS: (M+H)+=542.21. 1H NMR (500 MHz, CDCl3-MIX) δ ppm 7.57 (2H, d, J=7.15 Hz), 7.53 (1 H, d, J=8.80 Hz), 7.35-7.43 (3H, m), 7.31 (2H, t, J=7.70 Hz), 6.77 (2H, d, J=9.35 Hz), 6.01 (1H, d, J=8.80 Hz), 4.07-4.13 (1H, m), 3.75-3.81 (1H, m), 3.66-3.73 (1H, m), 3.58-3.66 (1H, m), 3.49-3.56 (1H, m), 2.98-3.03 (4H, m), 2.60-2.66 (1H, m), 2.56-2.60 (4H, m), 1.82-1.95 (2H, m), 1.66-1.76 (1H, m), 1.60 (1H, td, J=6.74, 3.57 Hz), 1.03 (6H, d, J=6.05 Hz).

Workup

  1. customThe reaction mixture was quenched with satd
  2. extractionNaHCO3, extracted twice with CH2Cl2
  3. concentrationconcentrated
  4. customThe residue was purified by prep-HPLC
  5. additionThe product containing fractions
  6. customwere collected
  7. extractionextracted with CH2Cl2
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e16db65f9cdc4a2383228cfad82ba515
Source dataset
uspto-grants-2013_11
Patent number
US08586751B2

Reaction notes

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