Methanol → HCID 178488597, compound

HRID 2174097Notes

Reaction equation

HRID 2174097 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](OCC)(=O)[CH:38]=[O:39].CO.[BH4-].[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][CH2:37][CH2:38][OH:39])[C:3]([F:6])([F:5])[F:4])=[N:8][C:9]=2[CH:15]=1)#[N:17]

Participants

6

Reactant 4

HCID 887MethanolHCID 70211Ethyl oxoacetateHCID 4311764Sodium borohydride3×HCID 178488596HCID 178488596, compound

Product 1

HCID 178488597HCID 178488597, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution 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 (50 mg, 0.100 mmol) and ethyl glyoxylate (50% in toluene) (39.7 μL, 0.200 mmol) in DCE (1.00 mL) was stirred at room temperature. After 50 minutes MeOH (1 mL) was added followed by NaBH4 (11.36 mg, 0.300 mmol). After 30 minutes additional NaBH4 (4 mg, 0.106 mmol) was added. After 25 more minutes additional NaBH4 (40 mg, 1.06 mmol) was added. After 15 more minutes the reaction was quenched with water, extracted twice with EtOAc, dried with MgSO4, filtered and concentrated. The resulting residue was purified by flash chromatography (0-80% EtOAc in heptanes) to provide the title compound. MS (ESI+) m/z 544.2 (M+H).

Workup

  1. customAfter 15 more minutes the reaction was quenched with water
  2. extractionextracted twice with EtOAc
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified by flash chromatography (0-80% EtOAc in heptanes)

Sources & evidence

ORD record
ord-962850b04eac451990e68041d579b415
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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