Triethylamine → 3-amino-6-(1-(ethylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)-N-(2-methylpyridin-4-yl)pyrazine-2-carboxamide

HRID 1959372노트

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HRID 1959372 반응식
[NH2:1][C:2]1[C:3]([C:19]([OH:21])=O)=[N:4][C:5]([C:8]2[CH2:9][CH2:10][N:11]([S:14]([CH2:17][CH3:18])(=[O:16])=[O:15])[CH2:12][CH:13]=2)=[CH:6][N:7]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.C(N(CC)CC)C.[CH3:41][C:42]1[CH:47]=[C:46]([NH2:48])[CH:45]=[CH:44][N:43]=1>CN(C1C=CN=CC=1)C>[NH2:1][C:2]1[C:3]([C:19]([NH:48][C:46]2[CH:45]=[CH:44][N:43]=[C:42]([CH3:41])[CH:47]=2)=[O:21])=[N:4][C:5]([C:8]2[CH2:9][CH2:10][N:11]([S:14]([CH2:17][CH3:18])(=[O:15])=[O:16])[CH2:12][CH:13]=2)=[CH:6][N:7]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 7286704-Amino-2-methylpyridineHCID 667448673-amino-6-(1-ethylsulfonyl-3,6-dihydro-2H-pyridin-4-yl)pyrazine-2-carboxylic acid

생성물 1

HCID 667454793-amino-6-(1-(ethylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)-N-(2-methylpyridin-4-yl)pyrazine-2-carboxamide수율 29.6%

시약·촉매·용매 1

HCID 142844-(Dimethylamino)pyridine촉매

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온도
100 °C

실험 절차

A solution of 3-amino-6-(1-ethylsulfonyl-3,6-dihydro-2H-pyridin-4-yl)pyrazine-2-carboxylic acid (79.87 mg, 0.255 mmol), CDI (82.92 mg, 0.511 mmoles), triethylamine (107 uL, 0.767 mmoles), and DMAP (1.56 mg, 0.012 mmol) was treated with 2-methylpyridin-4-amine (55.30 mg, 0.511 mmol). The reaction was allowed to stir at 100° C. for 16 hours, filtered and purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected, and freeze-dried to give the title compound (30.4 mg, 21% Yield). 1H NMR (400.0 MHz, DMSO) d 11.10 (s, 1H), 8.69-8.67 (m, 2H), 8.25-8.22 (m, 2H), 7.72 (s, 2H), 6.77 (d, J=3.3 Hz, 1H), 3.99 (d, J=2.9 Hz, 2H), 3.48 (t, J=5.7 Hz, 2H), 3.16 (q, J=7.4 Hz, 2H), 2.79 (s, 2H), 2.68 (s, 3H) and 1.25 (t, J=7.3 Hz, 3H) ppm; MS (ES+) 403.0

후처리

  1. filtrationfiltered
  2. custompurified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]
  3. customThe fractions were collected
  4. customfreeze-dried

출처 및 근거

ORD 기록
ord-29a5db25d33d4d818082bae0d52e2696
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410112B2

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