Acetic Acid → HCID 68736171, compound

HRID 240774Notes

Reaction equation

HRID 240774 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-30aef2ea952242b8b83a42e78ce2ae07
Source dataset
uspto-grants-2014_02
Patent number
US08648069B2

Reaction notes

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