Piperazine → N4-[3-Fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]-6-piperazin-1-ylpyrimidine-2,4-diamine

HRID 16455Notes

Reaction equation

HRID 16455 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]3[CH:22]=[CH:21][N:20]=[C:19]4[NH:23][CH:24]=[CH:25][C:18]=34)=[C:12]([F:26])[CH:11]=2)[CH:3]=1.C(N(C(C)C)C(C)C)C.[NH:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1>C(O)CCC>[F:26][C:12]1[CH:11]=[C:10]([NH:9][C:4]2[CH:3]=[C:2]([N:36]3[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]3)[N:7]=[C:6]([NH2:8])[N:5]=2)[CH:15]=[CH:14][C:13]=1[O:16][C:17]1[CH:22]=[CH:21][N:20]=[C:19]2[NH:23][CH:24]=[CH:25][C:18]=12

Participants

5

Reactant 3

HCID 4837PiperazineHCID 81531DiisopropylethylamineHCID 587332416-Chloro-N4-[3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]pyrimidine-2,4-diamine

Product 1

HCID 58733318N4-[3-Fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]-6-piperazin-1-ylpyrimidine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

75 mg (0.20 mmol) of 6-chloro-N4-[3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)-phenyl]pyrimidine-2,4-diamine (from example 60) are dissolved in 3 ml of 1-butanol. 0.35 ml of N-ethyldiisopropylamine and 70 mg (0.81 mmol) of piperazine are added, and the mixture is heated at reflux for 5 hours. The solvent is then removed under reduced pressure and the residue is purified by preparative HPLC.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 5 hours
  3. customThe solvent is then removed under reduced pressure
  4. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-5b15cd4817cc4ad0b74627a79094870d
Source dataset
uspto-grants-2010_06
Patent number
US07737153B2

Reaction notes

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