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

HRID 234290노트

반응식

HRID 234290 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, 1.0M 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 (El, 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-40b4561fbaf64ac397867cc75e417a25
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05594140

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