HCID 59432474, compound → HCID 59432386, compound

HRID 507143Notes

Reaction equation

HRID 507143 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH2:13][CH2:12][CH2:11][CH:10]([N:14]([C:21](=O)[C:22]2[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[C:24]([C:32]([F:35])([F:34])[F:33])[CH:23]=2)[C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[C:9]2[CH:37]=[C:38]([CH3:45])[C:39]([C:41]([F:44])([F:43])[F:42])=[CH:40][C:8]1=2)=[O:6])([CH3:3])[CH3:2]>C1COCC1>[CH:1]([O:4][C:5]([N:7]1[CH2:13][CH2:12][CH2:11][CH:10]([N:14]([CH2:21][C:22]2[CH:23]=[C:24]([C:32]([F:33])([F:34])[F:35])[CH:25]=[C:26]([C:28]([F:29])([F:30])[F:31])[CH:27]=2)[C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[C:9]2[CH:37]=[C:38]([CH3:45])[C:39]([C:41]([F:44])([F:43])[F:42])=[CH:40][C:8]1=2)=[O:6])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 59432474HCID 59432474, compound

Product 1

HCID 59432386HCID 59432386, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

Add a solution of borane-THF complex in THF (1.0 M, 0.2 mL, 0.2 mmol) to 5-[(3,5-Bis-trifluoromethyl-benzoyl)-pyridin-3-yl-amino]-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylic acid isopropyl ester (90.1 mg, 0.139 mmol) in THF (1.6 mL). Heat in a sealed tube (70° C.) for 14 h. Add saturated aqueous sodium bicarbonate (5 mL) and extract with EtOAc (3×5 mL). Dry (MgSO4), concentrate, and purify via column chromatography (silica gel; 10% to 20% to 25% EtOAc:hexanes) to give 19 mg (22%) of the title compound as a yellow solid. APCI MS m/z 634 [M+H]+.

Workup

  1. extractionAdd saturated aqueous sodium bicarbonate (5 mL) and extract with EtOAc (3×5 mL)
  2. dry with materialDry (MgSO4)
  3. concentrationconcentrate
  4. custompurify via column chromatography (silica gel; 10% to 20% to 25% EtOAc:hexanes)

Sources & evidence

ORD record
ord-edaa53b8946447f9868156079bd12d9d
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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