Trifluoroacetic acid → (6S,9R)-6-(2,3-difluorophenyl)-3-[1-(trifluoromethyl)cyclopropyl]-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepin-9-amine

HRID 133136Notes

Reaction equation

HRID 133136 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=1[C@H:16]1[CH2:22][N:21]2[C:23]([C:26]3([C:29]([F:32])([F:31])[F:30])[CH2:28][CH2:27]3)=[CH:24][N:25]=[C:20]2[C@H:19]([NH:33]C(=O)OC(C)(C)C)[CH2:18][CH2:17]1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:8][C:9]1[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=1[C@H:16]1[CH2:22][N:21]2[C:23]([C:26]3([C:29]([F:32])([F:30])[F:31])[CH2:28][CH2:27]3)=[CH:24][N:25]=[C:20]2[C@H:19]([NH2:33])[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 59734930tert-butyl {(6S,9R)-6-(2,3-difluorophenyl)-3-[1-(trifluoromethyl)cyclopropyl]-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepin-9-yl}carbamate2×

Product 1

HCID 67526453(6S,9R)-6-(2,3-difluorophenyl)-3-[1-(trifluoromethyl)cyclopropyl]-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepin-9-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2 mL) was added to a solution of tert-butyl {(6S,9R)-6-(2,3-difluorophenyl)-3-[1-(trifluoromethyl)cyclopropyl]-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepin-9-yl}carbamate (170 mg, 0.361 mmol, described in Intermediate 8) in CH2Cl2 (2 mL). After 1 h, saturated NaHCO3 was added and the mixture was extracted with dichloromethane (3×). The combined organic extracts were washed with saturated brine, dried over MgSO4, filtered and concentrated in vacuo to give the title compound. MS: m/z=372 (M+1).

Workup

  1. extractionthe mixture was extracted with dichloromethane (3×)
  2. washThe combined organic extracts were washed with saturated brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-899de9ef9848444aabfb05a95e67d7f0
Source dataset
uspto-grants-2008_06
Patent number
US07390798B2

Reaction notes

Loading…