Trifluoroacetic acid → 5-[3-(5-Amino-3-methyl-3,6-dihydro-2H-[1,4]oxazin-3-yl)-phenyl]-nicotinonitrile trifluoroacetate

HRID 1946932Notes

Reaction equation

HRID 1946932 reaction equation
C(OC(=O)[NH:7][C:8]1[CH2:9][O:10][CH2:11][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[CH:22]=[N:23][CH:24]=[C:25]([C:27]#[N:28])[CH:26]=3)[CH:16]=2)([CH3:14])[N:13]=1)(C)(C)C.[F:30][C:31]([F:36])([F:35])[C:32]([OH:34])=[O:33]>ClCCl>[F:30][C:31]([F:36])([F:35])[C:32]([OH:34])=[O:33].[NH2:7][C:8]1[CH2:9][O:10][CH2:11][C:12]([C:15]2[CH:16]=[C:17]([C:21]3[CH:22]=[N:23][CH:24]=[C:25]([CH:26]=3)[C:27]#[N:28])[CH:18]=[CH:19][CH:20]=2)([CH3:14])[N:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68153473HCID 68153473, compound

Product 1

HCID 681534915-[3-(5-Amino-3-methyl-3,6-dihydro-2H-[1,4]oxazin-3-yl)-phenyl]-nicotinonitrile trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (RS)-{5-[3-(5-cyano-pyridin-3-yl)-phenyl]-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-yl}-carbamic acid tert-butyl ester (49 mg, 0.13 mmol) in dichloromethane (1.5 ml) was treated with trifluoroacetic acid (1.03 ml, 13.3 mmol). The orange colored solution was stirred at room temperature for 30 minutes. For the workup, the solution was evaporated at high vacuum. Heptane was added to the oily residue, and the resulting suspension was evaporated at reduced pressure. After drying at high vacuum the title compound was obtained as a brown solid (49 mg, 98% of theory). MS (ISP): m/z=293.1 [M+H]+.

Workup

  1. customFor the workup, the solution was evaporated at high vacuum
  2. additionHeptane was added to the oily residue
  3. customthe resulting suspension was evaporated at reduced pressure
  4. dry with materialAfter drying at high vacuum the title compound
  5. customwas obtained as a brown solid (49 mg, 98% of theory)

Sources & evidence

ORD record
ord-11cece180369448ba9f2d29eaa3071b9
Source dataset
uspto-grants-2013_03
Patent number
US08399459B2

Reaction notes

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