Acetic Acid → HCID 68736171, compound

HRID 1752561Notes

Reaction equation

HRID 1752561 reaction equation
[CH2:1]([N:8]1[C:12]([CH:13]2[CH2:15][CH2:14]2)=[C:11]([C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[NH:21][N:20]=[C:19]3[NH2:25])[N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.[CH:30](=O)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C)C=O>[CH2:30]([NH:25][C:19]1[C:18]2[C:22](=[CH:23][CH:24]=[C:16]([C:11]3[N:10]=[N:9][N:8]([CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[C:12]=3[CH:13]3[CH2:15][CH2:14]3)[CH:17]=2)[NH:21][N:20]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 25165086HCID 25165086, compound

Product 1

HCID 68736171HCID 68736171, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 89B (18.3 mg, 0.05 mmol) in dimethylformamide (2 mL) was added acetic acid (15 mg, 0.25 mmol) and benzaldehyde (6.4 mg, 0.06 mmol). The reaction mixture was stirred at room temperature overnight. Sodium triacetoxyborohydride (NaBH(OAc)3, 32 mg, 0.15 mmol) was added to the mixture. The reaction was stirred at room temperature for 3 hours, concentrated and purified by reverse phase-HPLC (CH3CN/H2O/NH4OAc) to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 13.09 (s, 1H), 9.24 (s, 1H), 8.02-8.10 (m, 3H), 7.84-7.90 (m, 1H), 7.49-7.67 (m, 4H), 7.25-7.45 (m, 5H), 5.70 (s, 2H), 3.30 (s, 2H), 1.88-1.95 (m, 1H), 1.01-1.09 (m, 2H), 0.43 (d, J=4.04 Hz, 2H). MS (ESI+) m/z 421 (M+H)+.

Workup

  1. stirringThe reaction was stirred at room temperature for 3 hours
  2. concentrationconcentrated
  3. custompurified by reverse phase-HPLC (CH3CN/H2O/NH4OAc)

Sources & evidence

ORD record
ord-8c352a4a83de40c8b56b84175ed7ec22
Source dataset
uspto-grants-2015_10
Patent number
US09163007B2

Reaction notes

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