Acetic Acid → HCID 44546700, compound

HRID 1512929Notes

Reaction equation

HRID 1512929 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:25]=3[NH:24][CH:23]=[C:22]4[CH2:26]CC=O)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[CH3:30][NH:31][CH2:32][C:33](O)=O.[C:36]([OH:39])(=[O:38])[CH3:37].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:25]=3[NH:24][CH:23]=[C:22]4[CH2:26][CH2:33][CH2:32][N:31]([CH3:30])[CH2:37][C:36]([OH:39])=[O:38])[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1088SarcosineHCID 5049666Sodium triacetoxyborohydrideHCID 59146073HCID 59146073, compound

Product 1

HCID 44546700HCID 44546700, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of 3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propanal (D92) (100 mg), N-methylglycine (43 mg) and acetic acid (0.1 mL) in DCM (15 mL) was added sodium triacetoxyborohydride (103 mg). The reaction was stirred at 40° C. for 3 h. The mixture was cooled to room temperature and partitioned between DCM (25 mL) and water (25 mL). The organic phase was washed with water (25 mL), dried over anhydrous sodium sulphate and evaporated to give the crude product, which was purified by Mass Directed Auto Prep to afford N-{3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propyl}-N-methylglycine (E71) (80 mg, TFA salt). δH (DMSO-d6, 400 MHz): 1.37 (6H, d), 2.08 (2H, m), 2.80 (2H, t), 2.82 (3H, s), 3.18 (2H, t), 4.07 (2H, s), 4.89 (1H, m), 7.23 (1H, t), 7.33 (1H, t), 7.45 (1H, d), 7.84 (1H, d), 7.96 (1H, d), 8.36 (1H, d), 10.87 (1H, s). MS (ES): C26H27ClN4O4 requires 482; found 483.2 (M+H+).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. custompartitioned between DCM (25 mL) and water (25 mL)
  3. washThe organic phase was washed with water (25 mL)
  4. dry with materialdried over anhydrous sodium sulphate
  5. customevaporated
  6. customto give the crude product, which
  7. customwas purified by Mass Directed Auto Prep

Sources & evidence

ORD record
ord-94ae962e160e4d2f8ca404e39572c34a
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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