Ethylamine → N-Ethyl-5-[2-(6-methyl-pyridin-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-nicotinamide

HRID 1878597노트

반응식

HRID 1878597 반응식
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[N:9]=[C:10]([C:17]3[CH:18]=[N:19][CH:20]=[C:21]([CH:25]=3)[C:22](O)=[O:23])[C:11]3[CH:16]=[CH:15][NH:14][C:12]=3[N:13]=2)[CH:5]=[CH:4][CH:3]=1.[CH2:26]([NH2:28])[CH3:27].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CC#N>[CH2:26]([NH:28][C:22](=[O:23])[C:21]1[CH:25]=[C:17]([C:10]2[C:11]3[CH:16]=[CH:15][NH:14][C:12]=3[N:13]=[C:8]([C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=3)[N:9]=2)[CH:18]=[N:19][CH:20]=1)[CH3:27]

참가 물질

6

반응물 4

HCID 6341EthylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 687615905-[2-(6-methyl-pyridin-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-nicotinic acid2회

생성물 1

HCID 44194351N-Ethyl-5-[2-(6-methyl-pyridin-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-nicotinamide

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 5-[2-(6-methyl-pyridin-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-nicotinic acid (Intermediate 5) (1 eq, 0.143 mmol, 50 mg) in MeCN (3 ml), ethylamine (1 eq, 0.143 mmol, 6.6 mg), EDC hydrochloride (1.5 eq, 0.215 mmol, 42 mg), HOBt (1.2 eq, 0.172 mmol, 23 mg), and TEA (5 eq, 0.720 mmol, 0.1 ml) are added. The mixture is heated using microwave radiation at 140° C. for 20 min. The resulting precipitate is filtered off and washed with MeCN. Drying the solid in vacuum affords the title compound; [M+H]+=359; 1H-NMR (400 MHz, CD3OD): δ 9.55 (d, 1H), 9.15 (t, 1H), 9.12 (d, 1H), 8.47 (d, 1H), 7.86 (t, 1H), 7.67 (d, 1H), 7.36 (d, 1H), 6.99 (d, 1H), 3.50 (q, 2H), 2.68 (s, 3H), 1.29 (t, 3H).

후처리

  1. temperatureThe mixture is heated
  2. customat 140° C.
  3. customfor 20 min
  4. filtrationThe resulting precipitate is filtered off
  5. washwashed with MeCN
  6. customDrying the solid in vacuum

출처 및 근거

ORD 기록
ord-43286868491e4a4499317fd74e48ca52
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08314112B2

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