Acetic Acid → HCID 76902035, compound

HRID 1507019Notes

Reaction equation

HRID 1507019 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[C:5]([NH:7][CH2:8][CH:9]([OH:20])[CH2:10][N:11]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12]1)=[O:6].[O:24]1[CH2:29][CH2:28][C:27](=O)[CH2:26][CH2:25]1.CC(O)=O.[BH3-]C#N.[Na+]>CO>[OH:20][CH:9]([CH2:10][N:11]1[CH2:12][C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:19]1)[CH2:8][NH:7][C:5](=[O:6])[C:4]1[CH:21]=[CH:22][CH:23]=[C:2]([NH:1][CH:27]2[CH2:28][CH2:29][O:24][CH2:25][CH2:26]2)[CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 121599Tetrahydro-4H-pyran-4-oneHCID 5003444Sodium cyanoborohydrideHCID 76901841HCID 76901841, compound

Product 1

HCID 76902035HCID 76902035, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 3-amino-N-(2-hydroxy-3-(isoindolin-2-yl)propyl)benzamide (120 mg, 0.39 mmol) in MeOH (10 mL) was added dihydro-2H-pyran-4(3H)-one (78 mg, 0.78 mmol) and AcOH (0.05 mL). The mixture was stirred at 25° C. for 2 h. NaBH3CN (123 mg, 1.95 mmol) was added, and the resulting mixture was stirred at 25° C. for 16 h. The reaction mixture was concentrated, and the residue was dissolved in water, extracted with ethyl acetate, dried over sodium sulfate and concentrated. The crude product was purified by preparative HPLC purification. (22 mg, yield 14%) MS (ESI+) e/z: 396.2 [M+1]+. 1H NMR (MeOD, 400 MHz), δ ppm: 7.62-7.53 (m, 2H), 7.53-7.36 (m, 5H), 7.30-7.21 (m, 1H), 4.76-4.57 (m, 2H), 4.34-4.24 (m, 1H), 4.08-3.96 (m, 2H), 3.74-3.65 (m, 1H), 3.65-3.57 (m, 2H), 3.57-3.43 (m, 4H), 3.36-3.32 (m, 2H), 2.03-1.91 (m, 2H), 1.72-1.57 (m, 2H).

Workup

  1. stirringthe resulting mixture was stirred at 25° C. for 16 h
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in water
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified by preparative HPLC purification

Sources & evidence

ORD record
ord-283f50b2f12340d49e122ae4b982c37d
Source dataset
uspto-grants-2015_12
Patent number
US09221794B2

Reaction notes

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