Trifluoroacetic acid → (2R)-2-amino-N-{6-[(3-ethyl-1,2-benzisoxazol-4-yl)oxy]-3-pyridinyl}butanamide

HRID 527530Notes

Reaction equation

HRID 527530 reaction equation
[CH2:1]([C:3]1[C:7]2[C:8]([O:12][C:13]3[N:18]=[CH:17][C:16]([NH:19][C:20]([C@H:22]([NH:25]C(=O)OC(C)(C)C)[CH2:23][CH3:24])=[O:21])=[CH:15][CH:14]=3)=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][N:4]=1)[CH3:2].C(O)(C(F)(F)F)=O>ClCCl>[NH2:25][C@H:22]([CH2:23][CH3:24])[C:20]([NH:19][C:16]1[CH:17]=[N:18][C:13]([O:12][C:8]2[C:7]3[C:3]([CH2:1][CH3:2])=[N:4][O:5][C:6]=3[CH:11]=[CH:10][CH:9]=2)=[CH:14][CH:15]=1)=[O:21]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 679668201,1-dimethylethyl {(1R)-1-[({6-[(3-ethyl-1,2-benzisoxazol-4-yl)oxy]-3-pyridinyl}amino)carbonyl]propyl}carbamate2×

Product 1

HCID 86698417(2R)-2-amino-N-{6-[(3-ethyl-1,2-benzisoxazol-4-yl)oxy]-3-pyridinyl}butanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-dimethylethyl {(1R)-1-[({6-[(3-ethyl-1,2-benzisoxazol-4-yl)oxy]-3-pyridinyl}amino)carbonyl]propyl}carbamate (Intermediate 34, 4.4 mg) was dissolved in dichloromethane (1.0 ml) and, at 0° C., TFA (0.100 ml, 1.3 mmol) was added. The reaction mixture was stirred at that temperature for 2 hours. After removal of the volatiles, the residue was charged on a SCX cartridge and eluted with DCM/MeOH/NH3 (2.0 M in MeOH) to afford the title compound.

Workup

  1. customAfter removal of the volatiles
  2. additionthe residue was charged on a SCX cartridge
  3. washeluted with DCM/MeOH/NH3 (2.0 M in MeOH)

Sources & evidence

ORD record
ord-0a79af27b5e34334ac961ae961b2caa0
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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