Ethyl oxoacetate → HCID 178472699, compound

HRID 2174099Notes

Reaction equation

HRID 2174099 reaction equation
[NH2:1][C:2]([C:18]1[C:26]([O:27][CH3:28])=[CH:25][C:24]([CH3:29])=[C:23]2[C:19]=1[CH:20]=[CH:21][N:22]2[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])([C:7]1[NH:11][C:10]2[CH:12]=[CH:13][C:14]([C:16]#[N:17])=[CH:15][C:9]=2[N:8]=1)[C:3]([F:6])([F:5])[F:4].[C:37]([O:41][CH2:42][CH3:43])(=[O:40])[CH:38]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:16]([C:14]1[CH:13]=[CH:12][C:10]2[NH:11][C:7]([C:2]([C:18]3[C:26]([O:27][CH3:28])=[CH:25][C:24]([CH3:29])=[C:23]4[C:19]=3[CH:20]=[CH:21][N:22]4[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])([NH:1][CH2:38][C:37]([O:41][CH2:42][CH3:43])=[O:40])[C:3]([F:6])([F:5])[F:4])=[N:8][C:9]=2[CH:15]=1)#[N:17]

Participants

5

Reactant 3

HCID 70211Ethyl oxoacetateHCID 5049666Sodium triacetoxyborohydrideHCID 178488596HCID 178488596, compound

Product 1

HCID 178472699HCID 178472699, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of (±)-tert-butyl 4-(1-amino-1-(5-cyano-1H-benzo[d]imidazol-2-yl)-2,2,2-trifluoroethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 139-A) (117 mg, 0.234 mmol) in DCE (2.34 mL) was added ethyl glyoxylate (50% in toluene) (93 μL, 0.468 mmol) and this was stirred at 60° C. After 5 minutes this was cooled to room temperature, then sodium triacetoxyborohydride (298 mg, 1.405 mmol) was added and this was stirred again at 60° C. After stirring overnight the reaction was quenched with sat. aq. sodium bicarbonate, extracted with EtOAc, dried with MgSO4, filtered and concentrated. The resulting residue was purified by flash chromatography (0-50% EtOAc in heptanes) to provide the title compound. MS (ESI+) m/z 586.3 (M+H).

Workup

  1. temperatureAfter 5 minutes this was cooled to room temperature
  2. stirringthis was stirred again at 60° C
  3. stirringAfter stirring overnight the reaction
  4. customwas quenched with sat. aq. sodium bicarbonate
  5. extractionextracted with EtOAc
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting residue was purified by flash chromatography (0-50% EtOAc in heptanes)

Sources & evidence

ORD record
ord-babca2e958ab4d0783e2cb3f5dffa57a
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

Loading…