Propanal → HCID 11960632, compound

HRID 1987514Notes

Reaction equation

HRID 1987514 reaction equation
[CH3:1][C:2]1([C:7]2[NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[C:15]([C:16]([NH2:18])=[O:17])[C:9]=3[N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3]1.[CH:19](=O)[CH2:20][CH3:21].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[CH3:1][C:2]1([C:7]2[NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[C:15]([C:16]([NH2:18])=[O:17])[C:9]=3[N:8]=2)[CH2:6][CH2:5][N:4]([CH2:19][CH2:20][CH3:21])[CH2:3]1

Participants

5

Reactant 3

HCID 527PropanalHCID 5049666Sodium triacetoxyborohydrideHCID 11960631HCID 11960631, compound

Product 1

HCID 11960632HCID 11960632, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the free base of Example 10E (70 mg, 0.3 mmol) in methanol (5 mL) was treated with propionaldehyde (25 mg, 0.4 mmol) at room temperature overnight. Sodium triacetoxyborohydride (254 mg, 1.2 mmol) was then added and the solution was stirred at rt for 3 h. After concentration under vacuum, the residue was separated by HPLC (Zorbax C-8, 0.1% TFA/CH3CN/H2O) to give 55 mg of desired product. Yield: 35%. MS (APCI) m/z 287 (M+H)+; 1H NMR (500 MHz, CD3O): δ 0.89 (t, J=7.33 Hz, 2 H), 1.60 (s, 3 H), 1.63-1.77 (m, 2 H), 2.12-2.40 (m, 1 H), 2.59-2.73 (m, 1 H), 3.03-3.40 (m, 5 H), 3.69 (s, 1 H), 3.96-4.50 (m, 1 H), 7.21 (t, 1 H), 7.56 (s, 1 H), 7.76 (s, 1 H); Anal. Calcd for C16H22N4O.2.0 TFA: C, 46.70; H, 4.70; N, 10.89. Found: C, 46.89; H, 4.68; N, 10.98.

Workup

  1. concentrationAfter concentration under vacuum
  2. customthe residue was separated by HPLC (Zorbax C-8, 0.1% TFA/CH3CN/H2O)

Sources & evidence

ORD record
ord-976a5519cf8c4d6580c2ba3e6e92852a
Source dataset
uspto-grants-2009_06
Patent number
US07550603B2

Reaction notes

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