Trifluoroacetic acid → HCID 86727492, compound

HRID 519112Notes

Reaction equation

HRID 519112 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:15]=2[C:21]2[CH:34]=[C:33]3[C:24]([N:25]4[C:30]([CH2:31][O:32]3)=[N:29][NH:28][C:27](=[O:35])[C@H:26]4[CH3:36])=[CH:23][CH:22]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[C:37]([OH:43])([C:39]([F:42])([F:41])[F:40])=[O:38]>C(Cl)Cl>[F:40][C:39]([F:42])([F:41])[C:37]([OH:43])=[O:38].[F:20][C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([N:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[C:15]=1[C:21]1[CH:34]=[C:33]2[C:24]([N:25]3[C:30]([CH2:31][O:32]2)=[N:29][NH:28][C:27](=[O:35])[C@H:26]3[CH3:36])=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86727494HCID 86727494, compound

Product 1

HCID 86727492HCID 86727492, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[3-fluoro-2-((R)-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-7-yl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester (enantiomer 1, 0.070 g, 0.141 mmol) in DCM (3 mL) was added TFA (1 mL) and the reaction mixture was stirred at ambient temperature for 1 h. The solvent was removed in vacuo to give (R)-7-(2-fluoro-6-piperazin-1-yl-phenyl)-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one trifluoroacetic acid (0.06 g, 85%) as a solid. 1H NMR (CD3OD, 400 MHz): δ 7.36 (m, 1H), 7.27 (m, 2H), 7.18 (s, 1H), 6.96 (m, 2H), 4.87 (m, 1H), 4.66 (d, J=13.0 Hz, 2H), 3.08 (s, 8H), 1.51 (d, J=6.8 Hz, 3H). LC/MS (Table 1, Method 4) Rt=1.684 min; MS m/z: 396 [M+H]+. SFC (Table 1, Method 33) Rt=4.921 min.

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-925a5e1c5e0f4fde943868d0d5231c76
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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