HCID 67166311, compound → HCID 51034408, compound

HRID 593469Notes

Reaction equation

HRID 593469 reaction equation
C(OC([NH:8][C:9]1[CH2:10][C:11]([C:31](=[O:40])[N:32]([CH2:36][CH2:37][CH2:38][F:39])[CH2:33][CH2:34][CH3:35])=[CH:12][C:13]2[CH:19]=[CH:18][C:17]([C:20]3[CH:30]=[CH:29][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22][CH:21]=3)=[CH:16][C:14]=2[N:15]=1)=O)(C)(C)C>ClCCl.C(O)(C(F)(F)F)=O>[NH2:8][C:9]1[CH2:10][C:11]([C:31](=[O:40])[N:32]([CH2:36][CH2:37][CH2:38][F:39])[CH2:33][CH2:34][CH3:35])=[CH:12][C:13]2[CH:19]=[CH:18][C:17]([C:20]3[CH:30]=[CH:29][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22][CH:21]=3)=[CH:16][C:14]=2[N:15]=1

Participants

4

Reactant 1

HCID 67166311HCID 67166311, compound

Product 1

HCID 51034408HCID 51034408, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

The crude product from Step E was then taken up in 2 mls of dichloromethane and 1 ml of TFA, and stirred at room temperature for one hour. The mixture was concentrated under reduced pressure and the resulting crude product was taken up in DCM (10 mls) and concentrated ammonium hydroxide (5 mls) and stirred at room temperature for 15 minutes, then extracted with dichloromethane. The extracts were dried over sodium sulfate and concentrated under reduced pressure. Preparative thin layer chromatography (2×0.5 mm plates, 7% MeOH/DCM/0.5% NH4OH) afforded 17 mgs (36%) of ethyl 4-((1E,4E)-2-amino-4-((3-fluoropropyl)(propyl)carbamoyl)-3H-benzo[b]azepin-8-yl)benzoate. 1H NMR (400 MHz, CDCl3) δ 8.09-8.14 (m, 2H), 7.70-7.74 (m, 2H), 7.52-7.55 (m, 1H), 7.32-7.41 (m, 2H), 6.87 (m, 1H), 5.11 (br s, 1H), 4.57-4.63 (m, 1H), 4.46-4.52 (m, 1H), 4.37-4.45 (m, 2H), 3.57-3.73 (m, 2H), 3.42-3.55 (m, 2H), 2.82 (s, 2H), 1.99-2.15 (m, 2H), 1.62-1.76 (m, 2H), 1.38-1.45 (m, 3H), 0.89-0.98 (m, 3H); m/z (APCI-pos) M+1=452.2.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. extractionextracted with dichloromethane
  3. dry with materialThe extracts were dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-643cd0eecc654db9b86ce6b6cc06dd98
Source dataset
uspto-grants-2016_01
Patent number
US09242964B2

Reaction notes

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