Triethylamine → HCID 67297471, compound

HRID 629037Notes

Reaction equation

HRID 629037 reaction equation
Cl[C:2]1[C:7]([S:8][CH3:9])=[C:6]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[N:5]=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:24])=[CH:18][CH:17]=2)[N:3]=1.[CH3:32][S:33]([N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1)(=[O:35])=[O:34].C(N(CC)CC)C>CN(C=O)C>[CH3:32][S:33]([N:36]1[CH2:41][CH2:40][N:39]([C:2]2[C:7]([S:8][CH3:9])=[C:6]([N:10]3[CH2:11][CH2:12][O:13][CH2:14][CH2:15]3)[N:5]=[C:4]([C:16]3[CH:17]=[CH:18][C:19]([NH:22][C:23]([NH:25][C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)=[O:24])=[CH:20][CH:21]=3)[N:3]=2)[CH2:38][CH2:37]1)(=[O:35])=[O:34]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 7091611-(Methylsulfonyl)piperazineHCID 86673518HCID 86673518, compound

Product 1

HCID 67297471HCID 67297471, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-[4-(4-chloro-5-methylsulfanyl-6-morpholin-4-yl-pyrimidin-2-yl)-phenyl]-3-phenyl-urea (120 mg, 0.26 mmol.), 1-methanesulfonyl-piperazine (65 mg, 0.39 mmol, 1.5 eq.), triethylamine (40 mg, 0.39 mmol, 1.5 eq.), and DMF (4.0 ml) was added to the reaction vessel and flushed with argon. The reaction mixture was stirred at 80° C. for 5 hrs and then dried, and the solvent was evaporated. The reaction mixture was partitioned between EA and NH4Cl(aq), the organic layer was washed with brine, dried over MgSO4, filtered and evaporated in vacuo. The resulting residue was purified with flash chromatography on silica gel (Hexane/EtOAc 1:1) to give a pale yellow solid of 77.2 mg (50.3%).

Workup

  1. additionwas added to the reaction vessel
  2. customflushed with argon
  3. customdried
  4. customthe solvent was evaporated
  5. customThe reaction mixture was partitioned between EA and NH4Cl(aq)
  6. washthe organic layer was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe resulting residue was purified with flash chromatography on silica gel (Hexane/EtOAc 1:1)
  11. customto give a pale yellow solid of 77.2 mg (50.3%)

Sources & evidence

ORD record
ord-bbdebaedac9149a59c43492551c2af87
Source dataset
uspto-grants-2016_04
Patent number
US09315491B2

Reaction notes

Loading…