Water → HCID 178448991, compound

HRID 1644596

Reaction equation

HRID 1644596 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:26][CH:27]([CH3:29])[CH3:28])=[C:13]([C:15]2[NH:25][C:18]3=[N:19][CH:20]=[C:21]([CH:23]=O)[CH:22]=[C:17]3[N:16]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:30][CH:31]([CH3:34])[CH2:32][NH2:33].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>C(O)(=O)C.ClCCl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:26][CH:27]([CH3:28])[CH3:29])=[C:13]([C:15]2[NH:25][C:18]3=[N:19][CH:20]=[C:21]([CH2:23][NH:33][CH2:32][CH:31]([CH3:34])[CH3:30])[CH:22]=[C:17]3[N:16]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6558IsobutylamineHCID 5049666Sodium triacetoxyborohydrideHCID 178458533HCID 178458533, compound

Product 1

HCID 178448991HCID 178448991, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 21922555Acetic acid methylene chlorideSolvent

Procedure

A solution of 2-[5-(benzyloxy)-2-isopropoxyphenyl]-3H-imidazo[4,5-b]pyridine-6-carbaldehyde (50 mg) and 2-methylpropan-1-amine (14 mg) in 10% acetic acid-dichloromethane (2 ml) was stirred at room temperature for 20 min. Sodium triacetoxyborohydride (55 mg) was added, and the mixture was stirred at room temperature for 18 hr. Water was added to the reaction mixture, and the mixture was extracted with dichloromethane. The extract was washed with water and concentrated. The residue was purified by preparative HPLC. Saturated aqueous sodium hydrogencarbonate solution was added to the obtained fraction to neutralize the mixture, and the mixture was extracted with dichloromethane. The extract was concentrated to give the title compound (32 mg, yield 56%) as colorless crystals. melting point 101-103° C. purity 97%. M+H: 445. 1H NMR (CDCl3) δ: 0.92 (6H, dd, J=6.6, 1.7 Hz), 1.49 (6H, dd, J=5.9, 1.6 Hz), 1.70-1.85 (1H, m), 2.50 (2H, d, J=6.8 Hz), 3.97 (2H, s), 4.71-4.78 (1H, m), 5.15 (2H, s), 6.98-7.08 (2H, m), 7.31-7.50 (5H, m), 8.05 (1H, s), 8.18 (1H, s), 8.33 (1H, s).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe extract was washed with water
  3. concentrationconcentrated
  4. customThe residue was purified by preparative HPLC
  5. additionSaturated aqueous sodium hydrogencarbonate solution was added to the obtained fraction
  6. extractionthe mixture was extracted with dichloromethane
  7. concentrationThe extract was concentrated

Sources & evidence

ORD record
ord-8fde4093294841fc9628fa4abf0d91a0
Source dataset
uspto-grants-2012_02
Patent number
US08124617B2

Linked notes

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