HCID 57747428, compound → HCID 57747432, compound

HRID 386644Notes

Reaction equation

HRID 386644 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[CH:5]=[C:4]([CH3:14])[C:3]=1[S:15][C:16]1[C:17]2[N:40]([CH3:41])[CH:39]=[CH:38][C:18]=2[N:19]=[C:20]([N:22]([C:30]2[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][CH:31]=2)C(=O)OC(C)(C)C)[N:21]=1>C(O)(C(F)(F)F)=O>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[CH:10][N:11]=[CH:12][CH:13]=2)[CH:5]=[C:4]([CH3:14])[C:3]=1[S:15][C:16]1[C:17]2[N:40]([CH3:41])[CH:39]=[CH:38][C:18]=2[N:19]=[C:20]([NH:22][C:30]2[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][CH:31]=2)[N:21]=1

Participants

3

Reactant 1

HCID 57747428HCID 57747428, compound

Product 1

HCID 57747432HCID 57747432, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 4-(2,6-dimethyl-4-(pyridin-4-yl)phenylthio)-5-methyl-5H-pyrrolo[3,2-d]pyrimidin-2-yl4-cyanophenylcarbamate is treated with TFA (10 mL) at 25° C. for 2 h. TFA is removed and the obtained residue dissolved in ethyl acetate, and extracted with saturated aqueous NaHCO3 (×2). The organic layer is collected, concentrated, and the purified by chromatography (SiO2, 1:4 hexanes/EtOAc).

Workup

  1. customTFA is removed
  2. dissolutionthe obtained residue dissolved in ethyl acetate
  3. extractionextracted with saturated aqueous NaHCO3 (×2)
  4. customThe organic layer is collected
  5. concentrationconcentrated
  6. customthe purified by chromatography (SiO2, 1:4 hexanes/EtOAc)

Sources & evidence

ORD record
ord-575311de9e3d4a1b90b030d43a4e239b
Source dataset
uspto-grants-2013_02
Patent number
US08372852B2

Reaction notes

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