Diisopropylethylamine → (4-Methylpiperazin-1-yl)-[3-(2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)phenyl]methanone

HRID 2240121노트

반응식

HRID 2240121 반응식
[Cl:1][C:2]1[N:3]=[C:4]([NH:11][C:12]2[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=2)[C:15]([OH:17])=O)[C:5]2[S:10][CH2:9][CH2:8][C:6]=2[N:7]=1.CN(C(ON1N=[N:36][C:31]2C=[CH:33][CH:34]=[N:35][C:30]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:45](N(C(C)C)CC)(C)C.ClC1N=C(CCCN)C2S(=O)(=O)CCC=2N=1>CS(C)=O>[CH3:45][N:35]1[CH2:30][CH2:31][N:36]([C:15]([C:14]2[CH:18]=[CH:19][CH:20]=[C:12]([NH:11][C:4]3[C:5]4[S:10][CH2:9][CH2:8][C:6]=4[N:7]=[C:2]([Cl:1])[N:3]=3)[CH:13]=2)=[O:17])[CH2:33][CH2:34]1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 576001073-(2-Chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)benzoic acidHCID 86616274(2-chloro-5,5-dioxo-6,7-dihydro-5H-5lambda6-thieno[3,2-d]pyrimidin-4-yl)propylamine

생성물 1

HCID 86616277(4-Methylpiperazin-1-yl)-[3-(2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)phenyl]methanone수율 33%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

0.600 g (1.95 mmol) of 3-(2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)benzoic acid (I), 0.741 g (1.95 mmol) of O-(7-azabenzotriazol-1-yl-)—N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU), and 0.680 mL (3.90 mmol) of diisopropylethylamine are placed in 10 mL of dimethylsulfoxide, then stirred for 0.5 hours at ambient temperature. 0.220 mL (1.95 mmol) of methylpiperazine (II) is added, then the mixture is stirred for 3 hours at ambient temperature. Then the reaction mixture is concentrated by evaporation and the residue is combined with water. Any precipitate formed is suction filtered and dried. The crude product is purified by chromatography through a 50 g silica cartridge with ethyl acetate/methanol 8:2. 0.250 g of product III (33%) is obtained.

후처리

  1. stirringthe mixture is stirred for 3 hours at ambient temperature
  2. concentrationThen the reaction mixture is concentrated by evaporation
  3. customAny precipitate formed
  4. filtrationfiltered
  5. customdried
  6. customThe crude product is purified by chromatography through a 50 g silica cartridge with ethyl acetate/methanol 8:2

출처 및 근거

ORD 기록
ord-6b860059b7b540c99d1dc5142e858c0a
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07723341B2

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