Trifluoroacetic acid → HCID 58551277, compound

HRID 1908061Notes

Reaction equation

HRID 1908061 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:32]=[CH:31][C:9]2[N:10]3[C:28]([C:29]#[N:30])=[CH:27][CH:26]=[C:11]3[C:12]3([CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]3)[O:13][C:8]=2[CH:7]=1)(=[O:3])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]([O:4][CH2:5][C:6]1[CH:32]=[CH:31][C:9]2[N:10]3[C:28]([C:29]#[N:30])=[CH:27][CH:26]=[C:11]3[C:12]3([CH2:14][CH2:15][NH:16][CH2:17][CH2:18]3)[O:13][C:8]=2[CH:7]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67469186HCID 67469186, compound

Product 1

HCID 58551277HCID 58551277, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 7′-(bromomethyl)-1′-cyano-spiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine]-1-carboxylate (33.0 mg, 0.0720 mmol) and potassium acetate (35.3 mg, 0.360 mmol) were combined in DMF (0.5 mL) and the mixture was stirred at 80° C. for 18 hours. The mixture was taken up in NH4Cl (10 mL) and was extracted with CH2Cl2 (10 mL). Solvent was removed under reduced pressure and the residue was purified by column chromatography (0-10% EtOAc/CH2Cl2) to obtain tert-butyl 7′-(acetoxymethyl)-1′-cyano-spiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine]-1-carboxylate (19.5 mg, 62%) as a clear oil. ESI-MS m/z calc. 437.2. found 438.5 (M+1)+; Retention time 2.05 minutes (3 min run). tert-Butyl 7′-(acetoxymethyl)-1′-cyano-spiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine]-1-carboxylate was dissolved in CH2Cl2 (10 mL) before TFA (5.0 mL, 65 mmol) was added. The solvent was removed under reduced pressure to give (1′-cyanospiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine]-7′-yl)methyl acetate (15 mg, 62%). ESI-MS m/z calc. 337.1. found 338.3 (M+1)+; Retention time 1.16 minutes (3 min run).

Workup

  1. customRetention time 2.05 minutes (3 min run)
  2. additionwas added
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-250f3ea8546e466f92ed73fe25b95443
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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