Acetic Acid → Ethyl 4-(2-fluoro-4-methylanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate

HRID 917744

반응식

HRID 917744 반응식
Cl[C:2]1C=[C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=2[F:21])[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:3]=1.COS(OC)(=O)=O.C(N(CC)CC)C.CC(O)=O.[CH3:40][CH2:41][OH:42]>C(Cl)(Cl)Cl>[F:21][C:15]1[CH:16]=[C:17]([CH3:20])[CH:18]=[CH:19][C:14]=1[NH:13][C:11]1[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:3]([CH3:2])[C:41](=[O:42])[CH:40]=1

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 702EthanolHCID 6497Dimethyl SulfateHCID 8471TriethylamineHCID 23630706Ethyl 6-chloro-4-(2-fluoro-4-methylanilino)nicotinate

생성물 1

HCID 11738242Ethyl 4-(2-fluoro-4-methylanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate수율 84%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

Ethyl 6-chloro-4-(2-fluoro-4-methylanilino)nicotinate) was dissolved in CHCl3 and reacted with Me2SO4, followed by triethylamine, AcOH and EtOH as described for example 33, step B. Purification by recrystallisation (EtOAc/Hexane) afforded ethyl 4-(2-fluoro-4-methylanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate (84%); m.p. (EtOAc/Hexane) 148-150° C. 1H NMR [400 MHz, CDCl3] δ 9.17 (br s, 1H), 8.20 (s, 1H), 7.27-7.21 (m, 1H), 6.99-6.92 (m, 2H), 5.76 (s, 1H), 4.35 (q, J=7.1 Hz, 2H), 3.53 (s, 3H), 2.35 (s, 3H), 1.39 (t, J=7.1 Hz, 3H). LCMS (ACPI−) 303 (100%). Anal. Calcd for C16H17FN2O3: C, 63.2; H, 5.6; N, 9.2. Found C, 63.1; H, 5.7; N, 9.2.

후처리

  1. customPurification
  2. customby recrystallisation (EtOAc/Hexane)

출처 및 근거

ORD 기록
ord-3a497ae313104678980dca189f23acef
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07273877B2

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