Trifluoroacetic acid → (R)-3-amino-1-[3-(4-fluoro-phenyl)-4H,6H-1,2,5,10b-tetraaza-benzo[e]azulen-5-yl]-4-(2,4,5-trifluoro-phenyl)-butan-1-one

HRID 1253902Notes

Reaction equation

HRID 1253902 reaction equation
C(OC(=O)[NH:7][CH:8]([CH2:33][C:34]1[CH:39]=[C:38]([F:40])[C:37]([F:41])=[CH:36][C:35]=1[F:42])[CH2:9][C:10]([N:12]1[CH2:21][C:20]2[N:16]([N:17]=[N:18][C:19]=2[C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[C:15]2[CH:29]=[CH:30][CH:31]=[CH:32][C:14]=2[CH2:13]1)=[O:11])(C)(C)C.[F:44][C:45]([F:50])([F:49])[C:46]([OH:48])=[O:47]>C(Cl)Cl>[F:44][C:45]([F:50])([F:49])[C:46]([OH:48])=[O:47].[NH2:7][C@H:8]([CH2:33][C:34]1[CH:39]=[C:38]([F:40])[C:37]([F:41])=[CH:36][C:35]=1[F:42])[CH2:9][C:10]([N:12]1[CH2:21][C:20]2[N:16]([N:17]=[N:18][C:19]=2[C:22]2[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)[C:15]2[CH:29]=[CH:30][CH:31]=[CH:32][C:14]=2[CH2:13]1)=[O:11]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 68782199[3-[3-(4-fluoro-phenyl)-4H,6H-1,2,5,10b-tetraaza-benzo[e]azulen-5-yl]-3-oxo-1-(2,4,5-trifluoro-benzyl)-propyl]-carbamic Acid tert-butyl ester

Product 2

HCID 6422Trifluoroacetic acidHCID 44156146(R)-3-amino-1-[3-(4-fluoro-phenyl)-4H,6H-1,2,5,10b-tetraaza-benzo[e]azulen-5-yl]-4-(2,4,5-trifluoro-phenyl)-butan-1-oneYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of [3-[3-(4-fluoro-phenyl)-4H,6H-1,2,5,10b-tetraaza-benzo[e]azulen-5-yl]-3-oxo-1-(2,4,5-trifluoro-benzyl)-propyl]carbamic acid tert-butyl ester (28.0 mg, 0.047 mmol) in DCM (2 mL), was added trifluoroacetic acid (0.18 mL, 3 mL/mmol). The reaction mixture was stirred at r.t. for 1 h. After the completion of the reaction as confirmed by TLC, excess of trifluoroacetic acid and DCM were evaporated in vacuo to afford a gummy solid which was crystallized from hexane to afford trifluoroacetic acid salt of (R)-3-amino-1-[3-(4-fluoro-phenyl)-4H,6H-1,2,5,10b-tetraaza-benzo[e]azulen-5-yl]-4-(2,4,5-trifluoro-phenyl)-butan-1-one (25 mg, 87%).

Workup

  1. customAfter the completion of the reaction
  2. customwere evaporated in vacuo
  3. customto afford a gummy solid which
  4. customwas crystallized from hexane

Sources & evidence

ORD record
ord-51ecaa9e0e9f4ac9892fadcb4cb59c73
Source dataset
uspto-grants-2013_06
Patent number
US08455479B2

Reaction notes

Loading…