HCID 16718606, compound → HCID 178428240, compound

HRID 1042089Notes

Reaction equation

HRID 1042089 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-9ed4d68f41a14e83a79becd66a0e528c
Source dataset
uspto-grants-2013_10
Patent number
US08557833B2

Reaction notes

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