Diisopropylethylamine → HCID 178428246, compound

HRID 1253814Notes

Reaction equation

HRID 1253814 reaction equation
Cl[C:2]1[N:7]=[C:6]([S:8][C:9]2[CH:10]=[C:11]3[C:16](=[C:17]([F:19])[CH:18]=2)[N:15]=[C:14]([CH3:20])[CH:13]=[CH:12]3)[N:5]=[C:4]([NH:21][C:22]2[NH:26][N:25]=[C:24]([CH3:27])[CH:23]=2)[CH:3]=1.[CH3:28][N:29]1[CH2:34][CH2:33][CH:32]([N:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)[CH2:31][CH2:30]1.C(N(C(C)C)CC)(C)C>C(O)CCC>[F:19][C:17]1[CH:18]=[C:9]([S:8][C:6]2[N:5]=[C:4]([NH:21][C:22]3[NH:26][N:25]=[C:24]([CH3:27])[CH:23]=3)[CH:3]=[C:2]([N:38]3[CH2:37][CH2:36][N:35]([CH:32]4[CH2:33][CH2:34][N:29]([CH3:28])[CH2:30][CH2:31]4)[CH2:40][CH2:39]3)[N:7]=2)[CH:10]=[C:11]2[C:16]=1[N:15]=[C:14]([CH3:20])[CH:13]=[CH:12]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5663241-(1-Methyl-4-piperidinyl)piperazineHCID 178428227HCID 178428227, compound

Product 1

HCID 178428246HCID 178428246, compoundYield 30.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred mixture of 6-chloro-2-(8-fluoro-2-methylquinolin-6-ylthio)-N-(3-methyl-1H-pyrazol-5-yl)pyrimidin-4-amine (200 mg, 0.5 mmol), 1-(1-methylpiperidin-4-yl)piperazine (367 mg, 2 mmol) and diisopropylethylamine (194 mg, 1.5 mmol) in nBuOH (5 ml) was heated to 90° C. for 18 hours. The crude mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was further extracted with water. The combined organic layers were washed with brine, dried over MgSO4 and concentrated in vacuo. The resulting residue was triturated with cold acetonitrile, filtered and dried to afford the title compound as an off-white solid (83 mg, 30% yield).

Workup

  1. concentrationThe crude mixture was concentrated in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. extractionThe organic layer was further extracted with water
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was triturated with cold acetonitrile
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-4320808d815b4651a1d7eb6be1095d0a
Source dataset
uspto-grants-2013_06
Patent number
US08455507B2

Reaction notes

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