Dimethylamine → HCID 57761843, compound

HRID 230952Notes

Reaction equation

HRID 230952 reaction equation
[N:1]1([C:7]2[N:12]=[C:11]([C:13]3[CH:14]=[C:15]([CH2:19][CH2:20][CH2:21]OS(C)(=O)=O)[CH:16]=[CH:17][CH:18]=3)[CH:10]=[C:9]([N:27]3[CH2:32][CH2:31][N:30]([C:33]4[C:38]([C:39]([F:42])([F:41])[F:40])=[CH:37][CH:36]=[CH:35][N:34]=4)[CH2:29][CH2:28]3)[N:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:43][NH:44][CH3:45]>C1COCC1>[CH3:43][N:44]([CH3:45])[CH2:21][CH2:20][CH2:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([C:11]2[CH:10]=[C:9]([N:27]3[CH2:32][CH2:31][N:30]([C:33]4[C:38]([C:39]([F:42])([F:41])[F:40])=[CH:37][CH:36]=[CH:35][N:34]=4)[CH2:29][CH2:28]3)[N:8]=[C:7]([N:1]3[CH2:2][CH2:3][O:4][CH2:5][CH2:6]3)[N:12]=2)[CH:14]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 57761294HCID 57761294, compound

Product 1

HCID 57761843HCID 57761843, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve the crude methanesulfonic acid 3-(3-{2-morpholin-4-yl-6-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyrimidin-4-yl}-phenyl)-propyl ester obtained above in THF and heat with an excess of dimethylamine in a sealed tube at 55° C. Concentrate under reduced pressure and partition the residue between aqueous NaHCO3 and EtOAc. Dry the organic layer (Na2SO4) and concentrate under reduced pressure. Purify the residue using preparative plate TLC (MeOH/DCM eluent) to afford the title compound. 1H NMR (CDCl3): δ 1.17 (m, 2H), 2.27 (s, 6H), 2.37 (t, 2H), 2.72 (t, 2H), 3.40 (m, 4H), 3.80 (m, 8H), 3.87 (m, 4H), 6.37 (s, 1H), 7.03 (m, 1H), 7.25 (d, 1H, J=7.1 Hz), 7.35 (dd, 1H), 7.79 (m, 2H), 7.89 (d, 1H, J=7.87 Hz), 8.46 (d, 1H).

Workup

  1. concentrationConcentrate under reduced pressure
  2. custompartition the residue between aqueous NaHCO3 and EtOAc
  3. dry with materialDry the organic layer (Na2SO4)
  4. concentrationconcentrate under reduced pressure
  5. customPurify the residue

Sources & evidence

ORD record
ord-846b9a20f0c848c3bb962442fea16a67
Source dataset
uspto-grants-2009_07
Patent number
US07566712B2

Reaction notes

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