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4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → 4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (3-ethyl-5-fluoro-pyrrolo[2,3-b]pyridin-1-yl)-amide

HRID 2382121
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HRID 2382121 반응식
[CH3:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][N:5]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[N:3]=1.[CH2:17]([C:19]1[C:27]2[C:22](=[N:23][CH:24]=[C:25]([F:28])[CH:26]=2)[N:21]([NH2:29])[CH:20]=1)[CH3:18].C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>CN(C=O)C.C([O-])([O-])=O.[Na+].[Na+]>[CH2:17]([C:19]1[C:27]2[C:22](=[N:23][CH:24]=[C:25]([F:28])[CH:26]=2)[N:21]([NH:29][C:8]([C:7]2[C:2]([CH3:1])=[N:3][C:4]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)=[N:5][CH:6]=2)=[O:10])[CH:20]=1)[CH3:18]
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참가 물질

6

반응물 3

HCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 617020254-Methyl-2-(pyridin-2-yl)pyrimidine-5-carboxylic acidHCID 685555931H-Pyrrolo[2,3-b]pyridin-1-amine, 3-ethyl-5-fluoro-

생성물 1

HCID 591999554-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (3-ethyl-5-fluoro-pyrrolo[2,3-b]pyridin-1-yl)-amide수율 60%

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
HCID 10340Sodium Carbonate용매

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온도
40 °C

실험 절차

A solution of 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (490 mg, 2.28 mmol) and 3-ethyl-5-fluoropyrrolo[2,3-b]pyridin-1-ylamine (340 mg, 1.9 mmol) in DMF (6 mL) is stirred at 40° C. for 1 h. The mixture is treated with DMTMM (524 mg, 1.9 mmol) and stirred at 40° C. for 1 h. The mixture is diluted with saturated aqueous Na2CO3 (5 mL) and stirred for 5 min. The precipitate is collected by filtration and dried in vacuo to afford 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (3-ethyl-5-fluoro-pyrrolo[2,3-b]pyridin-1-yl)-amide (427 mg, 60%). MS: 377 (M+H); 1H NMR (300 MHz, DMSO-d6): δ 11.94 (s, NH, 1H), 9.14 (s, 1H), 8.81 (d, 1H), 8.47 (d, 1H), 8.30 (s, 1H), 8.03 (m, 2H), 7.61 (m, 2H), 2.81 (s, 3H), 2.75 (q, 2H), 1.29 (t, 3H).

후처리

  1. stirringstirred for 5 min
  2. filtrationThe precipitate is collected by filtration
  3. customdried in vacuo

출처 및 근거

ORD 기록
ord-5400c4e19afb4ebfb5683b68dd93bb07
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08258130B2

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