4-Methylmorpholine → 2-[(2-bromo-pyridin-4-ylmethyl)-amino]-N-(2-methyl-2H-indazol-6-yl)-benzamide

HRID 858946

반응식

HRID 858946 반응식
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][NH:9][C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12]([OH:14])=O)[CH:5]=[CH:4][N:3]=1.[CH3:19][N:20]1[CH:28]=[C:27]2[C:22]([CH:23]=[C:24]([NH2:29])[CH:25]=[CH:26]2)=[N:21]1.CN1CCOCC1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O.C(=O)(O)[O-].[Na+]>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][NH:9][C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12]([NH:29][C:24]2[CH:25]=[CH:26][C:27]3[C:22]([CH:23]=2)=[N:21][N:20]([CH3:19])[CH:28]=3)=[O:14])[CH:5]=[CH:4][N:3]=1

참가 물질

7

반응물 4

HCID 79724-MethylmorpholineHCID 5902202-Methyl-2H-indazol-6-amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 231189932-[(2-Bromo-pyridin-4-ylmethyl)-amino]benzoic Acid

생성물 1

HCID 231189722-[(2-bromo-pyridin-4-ylmethyl)-amino]-N-(2-methyl-2H-indazol-6-yl)-benzamide수율 96%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 516892Sodium Bicarbonate용매

실험 절차

0.500 g (1.6 mmol) of 2-[(2-bromo-pyridin-4-ylmethyl)-amino]-benzoic acid, 0.471 g (3.2 mmol) of 2-methyl-2H-indazol-6-ylamine, 0.4 ml (3.68 mmol) of N-methylmorpholine and 0.729 g (1.92 mmol) of O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate (HATU) in 25 ml of dimethylformamide are stirred for 16 hours at room temperature. The dimethylformamide is drawn off in an oil pump vacuum. The remaining residue is drawn off in saturated sodium bicarbonate solution. It is extracted three times with ethyl acetate, and the combined organic phases are dried, filtered and concentrated by evaporation. The residue is chromatographed on silica gel with a gradient that consists of hexane:acetone=100:0 to 50:50 as an eluant. 0.669 g (96% of theory) of 2-[(2-bromo-pyridin-4-ylmethyl)-amino]-N-(2-methyl-2H-indazol-6-yl)-benzamide is obtained in the form of a beige foam.

후처리

  1. extractionIt is extracted three times with ethyl acetate
  2. customthe combined organic phases are dried
  3. filtrationfiltered
  4. concentrationconcentrated by evaporation
  5. customThe residue is chromatographed on silica gel with a gradient that

출처 및 근거

ORD 기록
ord-a418da18ef7046f291dc2b0dfbc2f2ff
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07148357B2

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