1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → [4-(Furan-2-carbonyl)-piperazin-1-yl]-(4-{4-[4-(4-hydroxybutylsulfanyl)phenyl]pyrimidin-2-ylamino}phenyl)methanone

HRID 33459

반응식

HRID 33459 반응식
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][S:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]3[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=3)[N:14]=2)=[CH:9][CH:8]=1.[O:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[C:34]([N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1)=[O:35].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C1COCC1.C(Cl)Cl>[O:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[C:34]([N:36]1[CH2:37][CH2:38][N:39]([C:24]([C:23]2[CH:22]=[CH:21][C:20]([NH:19][C:15]3[N:14]=[C:13]([C:10]4[CH:9]=[CH:8][C:7]([S:6][CH2:5][CH2:4][CH2:3][CH2:2][OH:1])=[CH:12][CH:11]=4)[CH:18]=[CH:17][N:16]=3)=[CH:28][CH:27]=2)=[O:25])[CH2:40][CH2:41]1)=[O:35]

참가 물질

7

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 5502061-(2-Furoyl)piperazineHCID 219059924-{4-[4-(4-Hydroxybutylsulfanyl)phenyl]pyrimidin-2-ylamino}benzoic acid

생성물 1

HCID 21906001[4-(Furan-2-carbonyl)-piperazin-1-yl]-(4-{4-[4-(4-hydroxybutylsulfanyl)phenyl]pyrimidin-2-ylamino}phenyl)methanone수율 9%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

4-{4-[4-(4-Hydroxybutylsulfanyl)phenyl]pyrimidin-2-ylamino}benzoic acid (0.34 g, 0.86 mmol) was dissolved in THF (5 mL). To this solution was added 1-furoylpiperazine (0.170 g), EDCI (0.180 g), and HOBt (0.127 g). The mixture was stirred 12 h. The mixture was then diluted with CH2Cl2 (20 mL) and washed with 2% NaOH (aq, 30 mL), water (30 mL), and then brine (30 mL). The organic layer was dried (Na2SO4), filtered, and concentrated. The crude solid was subjected to preparatory HPLC (30-80 acetonitrile/water gradient, 20 min). The desired fractions were concentrated to remove most of the acetonitrile, and then the aqueous mixture was extracted with CH2Cl2/2% NaOH (aq). The organic layer was dried (Na2SO4), filtered, and concentrated to afford [4-(Furan-2-carbonyl)-piperazin-1-yl]-(4-{4-[4-(4-hydroxybutylsulfanyl)phenyl]pyrimidin-2-ylamino}phenyl)methanone (0.042 g, 9%): HPLC Retention Time; 10.07 min. (Method B) M+H=558.3.

후처리

  1. washwashed with 2% NaOH (aq, 30 mL), water (30 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customwas subjected to preparatory HPLC (30-80 acetonitrile/water gradient, 20 min)
  6. concentrationThe desired fractions were concentrated
  7. customto remove most of the acetonitrile
  8. extractionthe aqueous mixture was extracted with CH2Cl2/2% NaOH (aq)
  9. dry with materialThe organic layer was dried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated

출처 및 근거

ORD 기록
ord-06a50cbaf5a34e198126dd8819487382
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429599B2

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