Triethyl methanetricarboxylate → 2-hydroxy-4-oxo-7-(5-trifluoromethyl-pyridin-2-yl)-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carboxylic acid ethyl ester

HRID 68937

반응식

HRID 68937 반응식
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][C:12]3[N:15]=[C:16]([NH2:18])[S:17][C:11]=3[CH2:10]2)=[N:7][CH:8]=1.[CH:21]([C:32](OCC)=[O:33])([C:27](OCC)=[O:28])[C:22]([O:24][CH2:25][CH3:26])=[O:23]>C1(C)C(C)=CC=CC=1>[CH2:25]([O:24][C:22]([C:21]1[C:27](=[O:28])[N:15]2[C:16]([S:17][C:11]3[CH2:10][N:9]([C:6]4[CH:5]=[CH:4][C:3]([C:2]([F:19])([F:1])[F:20])=[CH:8][N:7]=4)[CH2:14][CH2:13][C:12]=32)=[N:18][C:32]=1[OH:33])=[O:23])[CH3:26]

참가 물질

4

반응물 2

HCID 80471Triethyl methanetricarboxylateHCID 735550495-(5-(Trifluoromethyl)pyridin-2-yl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-amine

생성물 1

HCID 1363377772-hydroxy-4-oxo-7-(5-trifluoromethyl-pyridin-2-yl)-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carboxylic acid ethyl ester수율 15.5%

시약·촉매·용매 1

HCID 7237O-Xylene용매

반응 조건

온도
145 °C

실험 절차

The mixture of 5-(5-trifluoromethyl-pyridin-2-yl)-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-ylamine (5.7 gm, 0.019 mol) and triethyl methantricarboxylate (16.1 ml, 0.076 mol) in xylene (100 ml) was heated at 140-150° C. for 6 hours. Xylene was evaporated and diethyl ether was then added and the suspension was stirred for 15 minutes. It was filtered and washed with ether. The crude solid was digested with dichloromethane (200 ml) and filtered to remove insoluble residue. Dichloromethane layer was distilled off under vacuum to give 1.3 gm of title compound.

후처리

  1. customXylene was evaporated
  2. additiondiethyl ether was then added
  3. filtrationIt was filtered
  4. washwashed with ether
  5. filtrationfiltered
  6. customto remove insoluble residue
  7. distillationDichloromethane layer was distilled off under vacuum

출처 및 근거

ORD 기록
ord-6e1bf009e1fe450b9247887b89e521b1
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822484B2

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