Trifluoroacetic acid → HCID 57520129, compound

HRID 593346Notes

Reaction equation

HRID 593346 reaction equation
COC1C=CC(C([NH:24][C:25]2[CH2:26][O:27][CH2:28][C@:29]([C:32]3[CH:37]=[C:36]([NH:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH:35]=[CH:34][C:33]=3[F:43])([CH3:31])[N:30]=2)(C2C=CC(OC)=CC=2)C2C=CC=CC=2)=CC=1.FC(F)(F)C(O)=O>ClCCl>[CH2:39]([NH:38][C:36]1[CH:35]=[CH:34][C:33]([F:43])=[C:32]([C@:29]2([CH3:31])[CH2:28][O:27][CH2:26][C:25]([NH2:24])=[N:30]2)[CH:37]=1)[CH2:40][CH2:41][CH3:42]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68107936HCID 68107936, compound

Product 1

HCID 57520129HCID 57520129, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [bis-(4-methoxy-phenyl)-phenyl-methyl]-[(R)-5-(5-butylamino-2-fluoro-phenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-amine (26 mg, 44.7 mol) in dichloromethane 2.5 ml) was treated at room temperature with trifluoroacetic acid (17.1 1, 223 mol) for 20 hours. The reaction mixture was evaporated at reduced pressure and the crude product purified by flash chromatography on silica gel using a gradient of dichloromethane/methanol=100/0 to 90/10 as the eluent. The title compound was obtained as a light yellow oil (58%); (calculated) C15H22FN3O [279.350]; (found) [M+H]+=280.

Workup

  1. customThe reaction mixture was evaporated at reduced pressure
  2. customthe crude product purified by flash chromatography on silica gel using a gradient of dichloromethane/methanol=100/0 to 90/10 as the eluent

Sources & evidence

ORD record
ord-e41e837ad301474f98402cbb8fe31498
Source dataset
uspto-grants-2016_01
Patent number
US09242943B2

Reaction notes

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