Trifluoroacetic acid → HCID 86727296, compound

HRID 518952Notes

Reaction equation

HRID 518952 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][CH:30]=[CH:29][CH:28]=2)[O:23][CH2:22][C:21]2[N:16]3[C@@H:17]([CH3:34])[C:18](=[O:33])[NH:19][N:20]=2)[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].[NH:8]1[CH2:9][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][CH:30]=[CH:29][CH:28]=2)[O:23][CH2:22][C:21]2[N:16]3[C@@H:17]([CH3:34])[C:18](=[O:33])[NH:19][N:20]=2)[CH2:11]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86727298HCID 86727298, compound

Product 1

HCID 86727296HCID 86727296, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(4(S)-methyl-3-oxo-7-phenyl-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 1), Rt=4.333 min., 0.252 g, 0.54 mmol) in TFA (4 mL) and DCM (24 mL) was stirred at ambient temperature for 3 h. The solvent was removed in vacuo to give 6-(azetidin-3-ylamino)-4(S)-methyl-7-phenyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one trifluoroacetic acid (Example #1-2, Enantiomer 2, SFC (Table 1, Method 1), Rt=5.572 min, 0.261 g, 100%) as yellow solid. LC/MS (Table 1, Method 5) Rt=2.117 min.; MS m/z: 364 [M+H]+

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-671dc86d791848489334062fb17cb376
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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