Trifluoroacetic acid → HCID 86727340, compound

HRID 518987Notes

Reaction equation

HRID 518987 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([NH:12][C:13]2[CH:14]=[C:15]3[C:24](=[CH:25][C:26]=2[C:27]2[CH:32]=[CH:31]C(Cl)=CC=2Cl)[O:23][CH2:22][C:21]2[N:16]3[C@@H:17]([CH3:36])[C:18](=[O:35])[NH:19][N:20]=2)[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].[NH:8]1[CH2:11][CH:10]([NH:12][C:13]2[CH:14]=[C:15]3[C:24](=[CH:25][C:26]=2[CH:27]2[CH2:32][CH2:31]2)[O:23][CH2:22][C:21]2[N:16]3[C@@H:17]([CH3:36])[C:18](=[O:35])[NH:19][N:20]=2)[CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86727342HCID 86727342, compound

Product 1

HCID 86727340HCID 86727340, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[7-(2,4-dichloro-phenyl)-4(S)-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino]-azetidine-1-carboxylic acid tert-butyl ester (Enantiomer 2, SFC (Table 1, Method 12) Rt=8.89 min., 0.280 g, 0.655 mmol) in DCM (9 mL) was added TFA (1.5 mL) and the reaction mixture was stirred for 2 h at ambient temperature. The solution was concentrated in vacuo to give 6-(azetidin-3-ylamino)-7-cyclopropyl-4(S)-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one trifluoroacetic acid (Example #64-2, Enantiomer 2, SFC (Table 1, Method 1) Rt=5.859 min., 0.275 g, 0.624 mmol, 95%). LC/MS (Table 1, Method 4) Rt=1.331 min.; MS m/z: 328 [M+H]+.

Workup

  1. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-e1f4ff928b684f46b76287e7742bc9d9
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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