HCID 66960277, compound → ethyl 4-((1E,4E)-2-amino-4-((3-hydroxypropyl)(propyl)carbamoyl)-3H-benzo[b]azepin-8-yl)benzoate

HRID 38022Notes

Reaction equation

HRID 38022 reaction equation
C(OC([NH:8][C:9]1[CH2:10][C:11]([C:31](=[O:47])[N:32]([CH2:36][CH2:37][CH2:38][O:39][Si](C(C)(C)C)(C)C)[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:47])[N:32]([CH2:36][CH2:37][CH2:38][OH: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 66960277HCID 66960277, compound

Product 1

HCID 51034747ethyl 4-((1E,4E)-2-amino-4-((3-hydroxypropyl)(propyl)carbamoyl)-3H-benzo[b]azepin-8-yl)benzoateYield 35.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Ethyl 4-((1E,4E)-2-(tert-butoxycarbonylamino)-4-((3-(tert-butyldimethylsilyloxy)propyl)(propyl)carbamoyl)-3H-benzo[b]azepin-8-yl)benzoate (0.050 g, 0.075 mmol) was dissolved in 2 mls of dichloromethane and 0.5 ml of TFA. After about one hour, the mixture was concentrated under reduced pressure and the resulting residue was then re-dissolved in dichloromethane and 1 ml of concentrated ammonium hydroxide added and the mixture vigorously stirred for 15 minutes. This mixture was then diluted with water, extracted with dichloromethane (2×), extracts dried over sodium sulfate and concentrated under reduced pressure. Preparative thin layer chromatography (2×0.5 mm plates, 10% MeOH/DCM/0.5% NH4OH) afforded 0.012 g (35%) of ethyl 4-((1E,4E)-2-amino-4-((3-hydroxypropyl)(propyl)carbamoyl)-3H-benzo[b]azepin-8-yl)benzoate. 1H NMR (400 MHz, CDCl3) δ 8.08-8.14 (m, 2H), 7.69-7.74 (m, 2H), 7.52-7.55 (m, 1H), 7.32-7.40 (m, 2H), 6.89 (s, 1H), 4.35-4.44 (m, 2H), 3.58-3.71 (m, 5H), 3.45-3.53 (m, 2H), 2.85 (s, 2H), 1.81-1.88 (m, 2H), 1.64-1.77 (m, 2H), 1.36-1.44 (m, 3H), 0.90-0.97 (m, 3H); m/z (APCI-pos) M+1=450.2.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. dissolutionthe resulting residue was then re-dissolved in dichloromethane
  3. addition1 ml of concentrated ammonium hydroxide added
  4. additionThis mixture was then diluted with water
  5. extractionextracted with dichloromethane (2×)
  6. dry with materialextracts dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c47adb05db33491e861bebfa67a888ce
Source dataset
uspto-grants-2013_09
Patent number
US08524702B2

Reaction notes

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