Trifluoroacetic acid → HCID 86727513, compound

HRID 519127Notes

Reaction equation

HRID 519127 reaction equation
C(OC([N:8]1[CH2:11][C:10]([CH3:34])([C@@H:12]([C:14]2[CH:15]=[C:16]3[C:25](=[CH:26][C:27]=2[C:28]([F:31])([F:30])[F:29])[O:24][CH2:23][C:22]2[N:17]3[C@H:18]([CH3:33])[C:19](=[O:32])[NH:20][N:21]=2)[CH3:13])[CH2:9]1)=O)(C)(C)C.[C:35]([OH:41])([C:37]([F:40])([F:39])[F:38])=[O:36]>C(Cl)Cl>[F:38][C:37]([F:40])([F:39])[C:35]([OH:41])=[O:36].[CH3:33][C@H:18]1[N:17]2[C:22]([CH2:23][O:24][C:25]3[C:16]2=[CH:15][C:14]([C@H:12]([C:10]2([CH3:34])[CH2:9][NH:8][CH2:11]2)[CH3:13])=[C:27]([C:28]([F:29])([F:31])[F:30])[CH:26]=3)=[N:21][NH:20][C:19]1=[O:32]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86727515HCID 86727515, compound

Product 1

HCID 86727513HCID 86727513, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-methyl-3-[(R)-1-((R)-4-methyl-3-oxo-7-trifluoromethyl-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl)-ethyl]-azetidine-1-carboxylic acid tert-butyl ester (diastereomer 1, 0.062 g, 0.128 mmol) in DCM (4 mL) was added TFA (1 mL) and the reaction mixture was stirred at ambient temperature for 1.5 h. The solvent was removed in vacuo to give (R)-4-methyl-6-[(R)-1-(3-methyl-azetidin-3-yl)-ethyl]-7-trifluoromethyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one trifluoroacetic acid (Example #147-1, Enantiomer 1, 0.060 g, 94%) as a solid. 1H NMR (CD3OD-d4, 400 MHz): δ 7.46 (s, 1H), 7 (s, 1H), 4.95 (m, 1H), 4.70 (d, J=13.2 Hz, 2H), 4.3 (d, J=10.8 Hz, 1H), 3.95 (d, J=10.8 Hz, 1H), 3.65 (t, J=10.0 Hz, 2H), 3.26 (m, 1H), 1.55 (s, 3H), 1.49 (d, J=7.2 Hz, 3H), 1.44 (d, J=7.2 Hz, 3H). LC/MS (Table 1, Method 4) Rt=1.741 min; MS m/z: 383 [M+H]+. SFC (Table 1, Method 36) Rt=4.264 min.

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-dcd71c241cc944eb8a1f735af68959b7
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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