Dimethylformamide → tert-Butyl 5-[(cis-3,5-dimethylpiperazino)carbonyl]imidazo[1,5-a]quinoline-3-carboxylate

HRID 1585156노트

반응식

HRID 1585156 반응식
[CH3:1][C:2]([CH3:5])([O-:4])[CH3:3].[K+].[CH3:7][C@H:8]1[NH:13][C@@H:12]([CH3:14])[CH2:11][N:10]([C:15]2[C:16](Cl)=[N:17][C:18]3[C:23]([C:24]=2[C:25](N)=O)=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:9]1.C[C:30]([C:33]1ON=C(C[N+]#[C-])[N:34]=1)(C)C.CN([CH:44]=[O:45])C.C1C[O:49]CC1>O>[CH3:14][C@H:12]1[NH:13][C@@H:8]([CH3:7])[CH2:9][N:10]([C:15]([C:24]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]3[CH:16]=[N:34][C:33]([C:44]([O:4][C:2]([CH3:5])([CH3:3])[CH3:1])=[O:45])=[C:30]3[CH:25]=2)=[O:49])[CH2:11]1

참가 물질

7

반응물 5

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 107257105-(1,1-Dimethylethyl)-3-isocyanomethyl-1,2,4-oxadiazoleHCID 23665647Potassium tert-butoxideHCID 86750212cis-3,5-Dimethylpiperazino 2-chloroquinoline-4-carboxamide

생성물 1

HCID 22869039tert-Butyl 5-[(cis-3,5-dimethylpiperazino)carbonyl]imidazo[1,5-a]quinoline-3-carboxylate

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Potassium tert-butoxide (2.6 ml, 1.0 M in THF) is added to a mixture of cis-3,5-dimethylpiperazino 2-chloroquinoline-4-carboxamide (X, 704 mg), tert-butyl isocyanoacetate (IX, 390 mg) and DMF (10 ml) at -78°. The mixture is stirred for 1 hr at -78° and is allowed to warm to 20-25° over several hours. After stirring at 20-25° for 16 hrs, water is added and the mixture extracted several times with ethyl acetate, the combined organic phases are dried over magnesium sulfate, filtered, and concentrated to provide a mixture of product and starting material, which is resubmitted to the above conditions (THF used instead of DMF). Purification of the resultant crude material by flash chromatography (silica gel; ethyl acetate/methanol (4/1)) provides the product. Recrystallization from hot ethyl acetate/hexane gives the desired title compound, mp 233-234°; IR (mineral oil) 1719, 1615, 1607, 1388, 1270, 1128 cm-1 ; NMR (CDCl3) 8.67, 7.95-8.15, 7.65-7.9, 7.54, 4.7-4.85, 3.35-3.55, 2.4-3.1, 1.68, 1.22 and 0.85-1.05 δ; MS (EI, m/e) 408, 351, 335, 307, 239, 195 and 113.

후처리

  1. temperatureto warm to 20-25° over several hours
  2. stirringAfter stirring at 20-25° for 16 hrs
  3. extractionthe mixture extracted several times with ethyl acetate
  4. dry with materialthe combined organic phases are dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto provide
  8. additiona mixture of product
  9. customPurification of the resultant crude material by flash chromatography (silica gel; ethyl acetate/methanol (4/1))
  10. customprovides the product
  11. customRecrystallization from hot ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-986b41a154374c1c8fcfeca96803f3ac
출처 데이터셋
uspto-grants-1999_08
특허 번호
US05935970

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