Trifluoroacetic acid → Thiophene-2-carboxylic acid (3-aza-bicyclo[3.1.0]hex-6-ylmethyl)-(3-fluoro-4-morpholin-4-yl-phenyl)-amide trifluoroacetic acid salt

HRID 1452939Notes

Reaction equation

HRID 1452939 reaction equation
C(OC([N:8]1[CH2:13][CH:12]2[CH:10]([CH:11]2[CH2:14][N:15]([C:23]2[CH:28]=[CH:27][C:26]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[C:25]([F:35])[CH:24]=2)[C:16]([C:18]2[S:19][CH:20]=[CH:21][CH:22]=2)=[O:17])[CH2:9]1)=O)(C)(C)C.[C:36]([OH:42])([C:38]([F:41])([F:40])[F:39])=[O:37]>C(Cl)Cl>[F:39][C:38]([F:41])([F:40])[C:36]([OH:42])=[O:37].[CH:10]12[CH:11]([CH2:14][N:15]([C:23]3[CH:28]=[CH:27][C:26]([N:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)=[C:25]([F:35])[CH:24]=3)[C:16]([C:18]3[S:19][CH:20]=[CH:21][CH:22]=3)=[O:17])[CH:12]1[CH2:13][NH:8][CH2:9]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 690366556-{[(3-Fluoro-4-morpholin-4-yl-phenyl)-(thiophene-2-carbonyl)-amino]methyl}-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester

Product 1

HCID 86597825Thiophene-2-carboxylic acid (3-aza-bicyclo[3.1.0]hex-6-ylmethyl)-(3-fluoro-4-morpholin-4-yl-phenyl)-amide trifluoroacetic acid salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 6-{[(3-Fluoro-4-morpholin-4-yl-phenyl)-(thiophene-2-carbonyl)-amino]methyl}-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester prepared above (640 mg, 1.28 mmol) in 6 mL of CH2Cl2 at room temperature was added 6 mL of TFA. The reaction stirred at room temperature for 1 hour. The mixture was concentrated under reduced pressure, taken up in toluene and concentrated again to yield 854 mg of the desired product. 400 MHz 1H NMR (CDCl3) δ 9.06 (brs, 1H), 8.62 (brs, 1H), 7.33-7.35 (m, 1H), 7.21-7.25 (m, 1H), 6.94-7.11 (m, 2H), 6.88-6.92 (m, 1H), 6.81-6.84 (m, 1H), 3.89-3.91 (m, 4H), 3.72 (d, J=7.05 Hz, 2H), 3.39-3.46 (m, 4H), 3.16-3.18 (m, 4H), 1.77 (brs, 2H), 1.35-1.37 (m, 1H); MS (M+1) 402.1

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. concentrationconcentrated again

Sources & evidence

ORD record
ord-7f735bab747341309192bb2887dc8c16
Source dataset
uspto-grants-2009_01
Patent number
US07473787B2

Reaction notes

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