Trifluoroacetic acid → HCID 44155672, compound

HRID 1253910Notes

Reaction equation

HRID 1253910 reaction equation
C(OC(=O)[NH: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](=[O:32])[N:11]1[CH2:20][C:19]2[N:15]([CH:16]=[N:17][C:18]=2[C:21]([N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[O:22])[C:14]2[CH:28]=[CH:29][CH:30]=[CH:31][C:13]=2[CH2:12]1)(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:11]1[CH2:20][C:19]2[N:15]([CH:16]=[N:17][C:18]=2[C:21]([N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[O:22])[C:14]2[CH:28]=[CH:29][CH:30]=[CH:31][C:13]=2[CH2:12]1)=[O:32]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 68777526HCID 68777526, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 44155672HCID 44155672, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To solution of (R)-[3-oxo-3-[3-(pyrrolidine-1-carbonyl)-4H,6H-2,5,10b-triaza-benzo-[e]azulen-5-yl]-1-(2,4,5-trifluoro-benzyl)-propyl]-carbamic acid tert-butyl ester (45 mg, 0.08 mmol) in DCM (5 mL) was added trifluoroacetic acid (0.24 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-(pyrrolidine-1-carbonyl)-4H,6H-2,5,10b-triaza-benzo[e]azulen-5-yl]-4-(2,4,5-trifluoro-phenyl)-butan-1-one (40 mg, 86%)

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-b7a178ee67d74f33b256256ffd964438
Source dataset
uspto-grants-2013_06
Patent number
US08455479B2

Reaction notes

Loading…