Diisopropylethylamine → HCID 25234792, compound

HRID 221222Notes

Reaction equation

HRID 221222 reaction equation
[CH:1]1(/[CH:6]=[C:7](\[C:11]2[CH:24]=[CH:23][C:22]3[S:21](=[O:26])(=[O:25])[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]([CH3:27])[C:13]=3[CH:12]=2)/[C:8]([OH:10])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:28][N:29]1[CH:33]=[CH:32][C:31]([NH2:34])=[N:30]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>[CH:1]1(/[CH:6]=[C:7](\[C:11]2[CH:24]=[CH:23][C:22]3[S:21](=[O:25])(=[O:26])[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]([CH3:27])[C:13]=3[CH:12]=2)/[C:8]([NH:34][C:31]2[CH:32]=[CH:33][N:29]([CH3:28])[N:30]=2)=[O:10])[CH2:5][CH2:4][CH2:3][CH2:2]1

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 59533864HCID 59533864, compound

Product 1

HCID 25234792HCID 25234792, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

480 mg of (E)-3-cyclopentyl-2-(10-methyl-5,5-dioxo-5,10-dihydrophenothiazin-2-yl)acrylic acid, 122 mg of commercial 1-methyl-1H-pyrazol-3-ylamine and 0.76 ml of N,N-diisopropylethylamine are dissolved in 7 ml of dimethylformamide. 571 mg of HATU and 204 mg of HOAT are added, and the mixture is stirred at room temperature for one hour. 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 360 mg of (E)-3-cyclopentyl-2-(10-methyl-5,5-dioxo-5,10-dihydrophenothiazin-2-yl)-N-(1-methyl-1H-pyrazol-3-yl)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-0843041a2fb54d90b01cae850540b496
Source dataset
uspto-grants-2012_06
Patent number
US08207146B2

Reaction notes

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