Trifluoroacetic acid → HCID 70355685, compound

HRID 538358Notes

Reaction equation

HRID 538358 reaction equation
C(OC(=O)[NH:7][C:8]1[C@:9]([CH3:37])([C:33]([F:36])([F:35])[F:34])[O:10][CH2:11][C@:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][C:22]([C:24]3[C:29]([NH2:30])=[CH:28][C:27]([C:31]#[N:32])=[CH:26][N:25]=3)=[O:23])[N:16]=2)([CH3:14])[N:13]=1)(C)(C)C.C(O)(C(F)(F)F)=O.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[NH2:7][C:8]1[C@:9]([CH3:37])([C:33]([F:36])([F:34])[F:35])[O:10][CH2:11][C@:12]([C:15]2[N:16]=[C:17]([NH:21][C:22]([C:24]3[C:29]([NH2:30])=[CH:28][C:27]([C:31]#[N:32])=[CH:26][N:25]=3)=[O:23])[CH:18]=[CH:19][CH:20]=2)([CH3:14])[N:13]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 68107996HCID 68107996, compound

Product 1

HCID 70355685HCID 70355685, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ((2R,5R)-5-{6-[(3-amino-5-cyano-pyridine-2-carbonyl)-amino]-pyridin-2-yl}-2,5-dimethyl-2-trifluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-yl)-carbamic acid tert-butyl ester (71 mg, 0.133 mmol) in DCM (3 ml) was added TFA (1 ml). After stirring for 1.5 h the mixture was poured onto 10% aq. Na2CO3 and extracted three times with DCM. The combined organic layers were dried with K2CO3, filtered and evaporated. The title compound (46 mg) was obtained after chromatography on silica gel (hexanes/15-25% (EtOAc/EtOH 9:1)) as a yellow solid. HPLC: RtH3=3.027 min; ESIMS: 434 [(M+H)+]; 1H-NMR (600 MHz, DMSO-d6): 10.23 (s, 1H), 8.25 (s, 1H), 8.06 (d, 1H), 7.85 (t, 1H), 7.69 (s, 1H), 7.36-7.27 (m, broad, 3H), 6.12-6.00, (s, broad, 2H), 3.94 (d, 1H), 3.76 (d, 1H), 1.42 (s, 3H), 1.34 (s, 3H).

Workup

  1. extractionextracted three times with DCM
  2. dry with materialThe combined organic layers were dried with K2CO3
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-4eef4967467c4fc5848871ceb8b27a2f
Source dataset
uspto-grants-2014_10
Patent number
US08865712B2

Reaction notes

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