Triethylamine → 4-(3-Chloro-4-methoxybenzylamino)-5-methoxycarbonyl-6-(4-hydroxypiperidin-1-yl)-2-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-7-yl)pyrimidine

HRID 917627

반응식

HRID 917627 반응식
C(S([C:10]1[C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:14]([N:20]2[CH2:25][CH2:24][CH:23]([OH:26])[CH2:22][CH2:21]2)[N:13]=[C:12]([N:27]2[CH2:32][CH2:31][N:30]3[CH:33]=[CH:34][N:35]=[C:29]3[CH2:28]2)[N:11]=1)=O)C1C=CC=CC=1.[Cl:36][C:37]1[CH:38]=[C:39]([CH:42]=[CH:43][C:44]=1[O:45][CH3:46])[CH2:40][NH2:41].C(N(CC)CC)C>CN(C)C(=O)C>[Cl:36][C:37]1[CH:38]=[C:39]([CH:42]=[CH:43][C:44]=1[O:45][CH3:46])[CH2:40][NH:41][C:10]1[C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:14]([N:20]2[CH2:21][CH2:22][CH:23]([OH:26])[CH2:24][CH2:25]2)[N:13]=[C:12]([N:27]2[CH2:32][CH2:31][N:30]3[CH:33]=[CH:34][N:35]=[C:29]3[CH2:28]2)[N:11]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 7380383-Chloro-4-methoxybenzylamineHCID 178483354-Benzylsulfinyl-5-methoxycarbonyl-6-(4-hydroxypiperidin-1-yl)-2-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-7-yl)pyrimidine

생성물 1

HCID 178483124-(3-Chloro-4-methoxybenzylamino)-5-methoxycarbonyl-6-(4-hydroxypiperidin-1-yl)-2-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-7-yl)pyrimidine

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

반응 조건

온도
110 °C

실험 절차

A mixture of 4-benzylsulfinyl-5-methoxycarbonyl-6-(4-hydroxypiperidin-1-yl)-2-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-7-yl)pyrimidine (prepared in the above (6)) 83 mg, 3-chloro-4-methoxybenzylamine 86 mg, triethylamine 51 mg and N,N-dimethylacetoamide 3 ml is stirred at 110° C. for 1 hour. The reaction mixture is diluted with ice water and extracted with ethyl acetate. The organic layer is washed, dried and concentrated in vacuo. The residue is separated with silica gel chromatography (solvent; ethyl acetate ethyl acetate:methanol=15:1→10:1) and crystallized from a mixture of methanol, ethyl acetate and isopropyl ether to give 4-(3-chloro-4-methoxybenzylamino)-5-methoxycarbonyl-6-(4-hydroxypiperidin-1-yl)-2-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-7-yl)pyrimidine as a colorless crystalline powder 43 mg.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer is washed
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue is separated with silica gel chromatography (solvent; ethyl acetate ethyl acetate:methanol=15:1→10:1)
  6. customcrystallized from a mixture of methanol, ethyl acetate and isopropyl ether

출처 및 근거

ORD 기록
ord-d8d27e5ae49b4865acd39eae4a309fdb
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07273868B2

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