HCID 16718606, compound → HCID 178428240, compound

HRID 1162156Notes

Reaction equation

HRID 1162156 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][C:8]2[CH:13]=[C:12]([N:14]3[CH2:17][CH2:16][CH2:15]3)[N:11]=[C:10]([S:18][C:19]3[CH:24]=[CH:23][C:22]([NH:25]C(=O)OC(C)(C)C)=[CH:21][CH:20]=3)[N:9]=2)[CH:3]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:25][C:22]1[CH:23]=[CH:24][C:19]([S:18][C:10]2[N:9]=[C:8]([NH:7][C:4]3[NH:5][N:6]=[C:2]([CH3:1])[CH:3]=3)[CH:13]=[C:12]([N:14]3[CH2:15][CH2:16][CH2:17]3)[N:11]=2)=[CH:20][CH:21]=1

Participants

3

Reactant 1

HCID 16718606HCID 16718606, compound

Product 1

HCID 178428240HCID 178428240, compound

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

tert-butyl 4-(4-(5-methyl-1H-pyrazol-3-ylamino)-6-(azetidin-1-yl)pyrimidin-2-ylthio)phenylcarbamate (prepared using method similar to that described for example 6) (2.53 g, 5.6 mmol) was dissolved in 1:1 TFA-DCM (20 mL) and the resulting solution allowed to stand overnight at room temperature. The solution was concentrated in vacuo. The residue was taken up in EtOAc and washed with saturated aqueous sodium bicarbonate solution (×2) then brine and dried over sodium sulfate. The resulting tan solid (1.8 g, 91%) [MS (ES+) 354) was used without further purification or characterization in the next step.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. washwashed with saturated aqueous sodium bicarbonate solution (×2)
  3. dry with materialbrine and dried over sodium sulfate
  4. customThe resulting tan solid (1.8 g, 91%) [MS (ES+) 354) was used without further purification or characterization in the next step

Sources & evidence

ORD record
ord-bc47f7545fa24d81ba702e3521e5fe2a
Source dataset
uspto-grants-2010_10
Patent number
US07820685B2

Reaction notes

Loading…