Diisopropylethylamine → HCID 25234794, compound

HRID 221225Notes

Reaction equation

HRID 221225 reaction equation
[O:1]=[S:2]1(=[O:28])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]2[CH:7]=[C:6](/[C:16](=[CH:20]\[CH:21]3[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]3)/[C:17](O)=[O:18])[CH:5]=[CH:4][C:3]1=2.[CH3:29][N:30]1[CH:34]=[CH:33][C:32]([NH2:35])=[N:31]1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=NC2N(O)N=NC=2C=1>CN(C)C=O.C(OCC)(=O)C>[O:28]=[S:2]1(=[O:1])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]2[CH:7]=[C:6](/[C:16](=[CH:20]\[CH:21]3[CH2:22][CH2:23][C:24](=[O:27])[CH2:25][CH2:26]3)/[C:17]([NH:35][C:32]3[CH:33]=[CH:34][N:30]([CH3:29])[N:31]=3)=[O:18])[CH:5]=[CH:4][C:3]1=2

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 1372541-Methyl-3-aminopyrazoleHCID 181649HOAtHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59533861HCID 59533861, compound

Product 1

HCID 25234794HCID 25234794, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

276 mg of (E)-2-(5,5-dioxo-5,10-dihydrophenothiazin-2-yl)-3-(4-oxocyclohexyl)acrylic acid, 101 mg of commercial 1-methyl-1H-pyrazol-3-ylamine and 0.61 ml of N,N-diisopropylethylamine are dissolved in 10 ml of dimethylformamide. 318 mg of HATU and 114 mg of HOAT are added, and the mixture stirred at room temperature for two hours. The reaction mixture is then diluted by addition of 100 ml of ethyl acetate and washed five times with in each case 30 ml of water. The organic phase is dried over MgSO4, and the solvent is then removed under reduced pressure. The residue is purified on silica gel using the mobile phase n-heptane (100%)=>:ethyl acetate (100%). This gives 134 mg of (E)-2-(5,5-dioxo-5,10-dihydrophenothiazin-2-yl)-N-(1-methyl-1H-pyrazol-3-yl)-3-(4-oxocyclohexyl)acrylamide.

Workup

  1. washwashed five times with in each case 30 ml of water
  2. dry with materialThe organic phase is dried over MgSO4
  3. customthe solvent is then removed under reduced pressure
  4. customThe residue is purified on silica gel using the mobile phase n-heptane (100%)=>

Sources & evidence

ORD record
ord-d1ccd739cf6641b2b4d3f856f88f3bf5
Source dataset
uspto-grants-2012_06
Patent number
US08207146B2

Reaction notes

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