Potassium Acetate → HCID 67469186, compound

HRID 1908060Notes

Reaction equation

HRID 1908060 reaction equation
Br[CH2:2][C:3]1[CH:29]=[CH:28][C:6]2[N:7]3[C:25]([C:26]#[N:27])=[CH:24][CH:23]=[C:8]3[C:9]3([CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]3)[O:10][C:5]=2[CH:4]=1.[C:30]([O-:33])(=[O:32])[CH3:31].[K+]>CN(C=O)C.[NH4+].[Cl-]>[C:30]([O:33][CH2:2][C:3]1[CH:29]=[CH:28][C:6]2[N:7]3[C:25]([C:26]#[N:27])=[CH:24][CH:23]=[C:8]3[C:9]3([CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]3)[O:10][C:5]=2[CH:4]=1)(=[O:32])[CH3:31]

Participants

5

Reactant 2

HCID 517044Potassium AcetateHCID 58550944HCID 58550944, compound

Product 1

HCID 67469186HCID 67469186, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
80 °C

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. extractionwas extracted with CH2Cl2 (10 mL)
  2. customSolvent was removed under reduced pressure
  3. customthe residue was purified by column chromatography (0-10% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-f858284da29440e1b4d1f7d630e72ab1
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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