Methanol → HCID 44155564, compound

HRID 1253891Notes

Reaction equation

HRID 1253891 reaction equation
C(OC(=O)[NH:7][CH:8]([CH2:27][C:28]1[CH:33]=[C:32]([F:34])[C:31]([F:35])=[CH:30][C:29]=1[F:36])[CH2:9][C:10]([N:12]1[CH2:21][C:20]2[N:16]([CH:17]=[N:18][N:19]=2)[C:15]2[CH:22]=[C:23]([F:26])[CH:24]=[CH:25][C:14]=2[CH2:13]1)=[O:11])(C)(C)C.[F:38][C:39]([F:44])([F:43])[C:40]([OH:42])=[O:41].CO>C(Cl)Cl>[F:38][C:39]([F:44])([F:43])[C:40]([OH:42])=[O:41].[NH2:7][C@H:8]([CH2:27][C:28]1[CH:33]=[C:32]([F:34])[C:31]([F:35])=[CH:30][C:29]=1[F:36])[CH2:9][C:10]([N:12]1[CH2:21][C:20]2[N:16]([CH:17]=[N:18][N:19]=2)[C:15]2[CH:22]=[C:23]([F:26])[CH:24]=[CH:25][C:14]=2[CH2:13]1)=[O:11]

Participants

6

Reactant 3

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 66799768HCID 66799768, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 44155564HCID 44155564, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [3-(9-fluoro-4H,6H-2,3,5,10b tetraaza-benzo[e]-azulen-5-yl)-3-oxo-1-(2,4,5-trifluoro-benzyl)-propyl]-carbamic acid-tert-butyl ester, (2.04 g, 3.93 mmol); in dry DCM (12 mL) was added trifluoroacetic acid (11.79 mL, 3 mL/mmol) at 0° C. The reaction mixture was stirred at r.t. for 2 h under argon. After completion of the reaction as confirmed by TLC, methanol (2×5 mL) was added and the reaction mixture was evaporated under vacuo to remove excess of solvent and trifluoroacetic acid. The remaining solvents were removed under vacuo to obtain trifluoroacetic acid salt of (R)-3-amino-1-(9-fluoro-4H,6H-2,3,5,10b-tetraaza-benzo[e]azulen-5-yl)-4-(2,4,5-trifluoro-phenyl)-butan-1-one as a white solid (1.82 g, 3.42 mmol, 87%).

Workup

  1. customAfter completion of the reaction
  2. additionwas added
  3. customthe reaction mixture was evaporated under vacuo
  4. customto remove excess of solvent and trifluoroacetic acid
  5. customThe remaining solvents were removed under vacuo

Sources & evidence

ORD record
ord-c5580a6dfcc44027b42eb98fd1a1baa4
Source dataset
uspto-grants-2013_06
Patent number
US08455479B2

Reaction notes

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