Diisopropylethylamine → 2-(5,5-Dioxo-5,10-dihydrophenothiazin-2-yl)-n-(1-methyl-1h-pyrazol-3-yl)-3-(tetrahydropyran-4-yl)propionamide

HRID 14997

반응식

HRID 14997 반응식
[O:1]=[S:2]1(=[O:27])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]2[CH:7]=[C:6]([CH:16]([CH2:20][CH:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[C:17]([OH:19])=O)[CH:5]=[CH:4][C:3]1=2.[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>[O:1]=[S:2]1(=[O:27])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]2[CH:7]=[C:6]([CH:16]([CH2:20][CH:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)[C:17]([NH:34][C:31]3[CH:32]=[CH:33][N:29]([CH3:28])[N:30]=3)=[O:19])[CH:5]=[CH:4][C:3]1=2

참가 물질

8

반응물 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 580242292-(5,5-Dioxo-5,10-dihydrophenothiazin-2-yl)-3-(tetrahydropyran-4-yl)propionic acid

생성물 1

HCID 580242602-(5,5-Dioxo-5,10-dihydrophenothiazin-2-yl)-n-(1-methyl-1h-pyrazol-3-yl)-3-(tetrahydropyran-4-yl)propionamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

600 mg of 2-(5,5-dioxo-5,10-dihydrophenothiazin-2-yl)-3-(tetrahydropyran-4-yl)propionic acid, 120 mg of commercially available 1-methyl-1H-pyrazole-3-amine and 729 μl of N,N-diisopropylethylamine are dissolved in 5 ml of dimethylformamide. 561 mg of HATU and 200 mg of HOAT are added, and the mixture is stirred at room temperature for two hours. The reaction mixture is then diluted by addition of 200 ml of ethyl acetate and washed three times with in each case 50 ml of water and saturated sodium chloride solution. The organic phase is dried over MgSO4, and the solvent is then removed under reduced pressure. The residue is purified by RP-HPLC. This gives 200 mg of 2-(5,5-dioxo-5,10-dihydrophenothiazin-2-yl)-N-(11-methyl-1H-pyrazol-3-yl)-3-(tetrahydropyran-4-yl)propionamide as a colorless lyophilisate.

후처리

  1. washwashed three times with in each case 50 ml of water and saturated sodium chloride solution
  2. dry with materialThe organic phase is dried over MgSO4
  3. customthe solvent is then removed under reduced pressure
  4. customThe residue is purified by RP-HPLC

출처 및 근거

ORD 기록
ord-6d934af18b0a4f2baa267241da828b8e
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732440B2

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