Sodium Bicarbonate → (E)-N-(4-amino-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-8-yl)-4-(dimethylamino)-2-butenamide

HRID 336146노트

반응식

HRID 336146 반응식
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[C:27]([C:35]2[C:36]3[C:48]([NH2:49])=[N:47][CH:46]=[N:45][C:37]=3[N:38]3[C:43]=2[CH2:42][CH2:41][CH:40]([NH2:44])[CH2:39]3)[CH:26]=1.Cl.[CH3:51][N:52]([CH3:59])[CH2:53]/[CH:54]=[CH:55]/[C:56](O)=[O:57].C(=O)(O)[O-].[Na+]>CN(C=O)C>[NH2:49][C:48]1[C:36]2[C:35]([C:27]3[CH:26]=[N:25][C:34]4[C:29]([CH:28]=3)=[CH:30][CH:31]=[CH:32][CH:33]=4)=[C:43]3[N:38]([C:37]=2[N:45]=[CH:46][N:47]=1)[CH2:39][CH:40]([NH:44][C:56](=[O:57])/[CH:55]=[CH:54]/[CH2:53][N:52]([CH3:59])[CH3:51])[CH2:41][CH2:42]3

참가 물질

6

반응물 4

HCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 45358758(2E)-4-(Dimethylamino)-2-butenoic acid hydrochlorideHCID 867112835-(Quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizine-4,8-diamine

생성물 1

HCID 71721577(E)-N-(4-amino-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-8-yl)-4-(dimethylamino)-2-butenamide수율 54.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

HATU (10.3 mg) and 5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizine-4,8-diamine (8.8 mg) obtained in Step 11 of Example 1 were added to a solution of trans-4-dimethylaminocrotonic acid hydrochloride (4.5 mg) in DMF (0.5 ml) at room temperature. After being stirred for 1 hour at the same temperature, the mixture was poured into a saturated aqueous sodium bicarbonate solution, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure. The resulting residue was purified by preparative thin-layer chromatography (produced by Wako, NH2 silica-gel 60 F254 plate, developing solvent: chloroform/methanol) to obtain the title compound as a light-yellow solid (6.4 mg).

후처리

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. distillationthe solvent was then distilled off under reduced pressure
  4. customThe resulting residue was purified by preparative thin-layer chromatography (produced by Wako, NH2 silica-gel 60 F254 plate, developing solvent: chloroform/methanol)

출처 및 근거

ORD 기록
ord-9d74c321996546108d8d7e0fe803c386
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889666B2

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