Trifluoroacetic acid → (S)-(3,5-bistrifluoromethylbenzyl)-(2-methyl-2H-tetrazol-5-yl)-(7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)amine

HRID 507036Notes

Reaction equation

HRID 507036 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]([F:52])([F:51])[C:10]1[CH:11]=[C:12]([CH:44]=[C:45]([C:47]([F:50])([F:49])[F:48])[CH:46]=1)[CH2:13][N:14]([C:38]1[N:39]=[N:40][N:41]([CH3:43])[N:42]=1)[C@H:15]1[CH2:21][CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[C:17]2[CH:29]=[C:30]([C:34]([F:37])([F:36])[F:35])[C:31]([CH3:33])=[CH:32][C:16]1=2.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:51][C:9]([F:8])([F:52])[C:10]1[CH:11]=[C:12]([CH:44]=[C:45]([C:47]([F:50])([F:48])[F:49])[CH:46]=1)[CH2:13][N:14]([C:38]1[N:39]=[N:40][N:41]([CH3:43])[N:42]=1)[C@H:15]1[CH2:21][CH2:20][CH2:19][NH:18][C:17]2[CH:29]=[C:30]([C:34]([F:35])([F:36])[F:37])[C:31]([CH3:33])=[CH:32][C:16]1=2

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 11585492(S)-tert-Butyl 5-[(3,5-bistrifluoromethylbenzyl)-(2-methyl-2H-tetrazol-5-yl)amino]-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate

Product 1

HCID 59432408(S)-(3,5-bistrifluoromethylbenzyl)-(2-methyl-2H-tetrazol-5-yl)-(7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)amineYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add trifluoroacetic acid (10 mL) to a solution of (S)-tert-butyl 5-[(3,5-bistrifluoromethylbenzyl)-(2-methyl-2H-tetrazol-5-yl)amino]-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate (2.04 g, 3.13 mmol) in methylene chloride (50 mL) at 0° C. under nitrogen. Warm the mixture to room temperature, stir for 8 h and pour the mixture into saturated aqueous sodium bicarbonate solution (200 mL). Extract the mixture with methylene chloride (200 mL) and wash the combined organic extracts with brine (50 mL), dry over anhydrous sodium sulfate and filter. Remove the solvent under reduced pressure to provide the title compound as a colorless oil (1.73 g, >99%), which is used in the next step without purification. APCI MS m/z 553 (M+H)+.

Workup

  1. extractionExtract the mixture with methylene chloride (200 mL)
  2. washwash the combined organic extracts with brine (50 mL)
  3. dry with materialdry over anhydrous sodium sulfate
  4. filtrationfilter
  5. customRemove the solvent under reduced pressure

Sources & evidence

ORD record
ord-a5a407774c004243bc449609cc1ba51e
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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