Acetic Acid → HCID 44548575, compound

HRID 1512911Notes

Reaction equation

HRID 1512911 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[N:24](C)[CH:23]=[C:22]4C=O)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[CH3:29][NH:30][CH2:31][C:32]([OH:34])=[O:33].[C:35](O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[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[CH2:29][N:30]([CH3:35])[CH2:31][C:32]([OH:34])=[O:33])[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1088SarcosineHCID 5049666Sodium triacetoxyborohydrideHCID 591461277-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indole-3-carbaldehyde

Product 1

HCID 44548575HCID 44548575, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
40 °C

Procedure

To a stirred solution of 7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indole-3-carbaldehyde (D61) (200 mg), N-methylglycine (93 mg) and acetic acid (32 mg) in DCM (10 mL) was added NaBH(OAc)3 (223 mg). The reaction was stirred at 40° C. overnight. After cooled to room temperature, the reaction mixture was diluted with DCM (10 mL), washed with water (20 mL) and aqueous saturated sodium bicarbonate (20 mL). The organic phase was separated and dried over anhydrous sodium sulphate. After concentration, the residue was purified by Mass Directed Auto Prep to afford N-{[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]methyl}-N-methylglycine (E52) (210 mg, TFA salt). δH (DMSO-d6, 400 MHz): 1.36 (6H, d), 2.80 (3H, s), 4.01 (2H, s), 4.57 (2H, s), 4.90 (1H, m), 7.35 (1H, t), 7.46 (1H, d), 7.75 (1H, d), 8.01 (1H, d), 8.07 (1H, d), 8.21 (1H, dd), 8.39 (1H, d), 11.48 (1H, br s). MS (ES): C23H23ClN4O4 requires 454; found 366.1 (M—C3H6NO2+).

Workup

  1. temperatureAfter cooled to room temperature
  2. washwashed with water (20 mL) and aqueous saturated sodium bicarbonate (20 mL)
  3. customThe organic phase was separated
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationAfter concentration
  6. customthe residue was purified by Mass Directed Auto Prep

Sources & evidence

ORD record
ord-082c98d893da417ca8a67572b899bc7a
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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