1,1'-Carbonyldiimidazole → 1-(3,3-Diphenylpropyl)-1-isopropyl-3-(4-(4-(methylsulfonamido)phenyl)thiazol-2-yl)urea

HRID 2190327노트

반응식

HRID 2190327 반응식
C1N=CN([C:6](N2C=NC=C2)=[O:7])C=1.[NH2:13][C:14]1[S:15][CH:16]=[C:17]([C:19]2[CH:24]=[CH:23][C:22]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])=[CH:21][CH:20]=2)[N:18]=1.[CH:30]([NH:33][CH2:34][CH2:35][CH:36]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([CH3:32])[CH3:31]>CN(C1C=CN=CC=1)C.CN(C=O)C>[C:43]1([CH:36]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH2:35][CH2:34][N:33]([CH:30]([CH3:32])[CH3:31])[C:6]([NH:13][C:14]2[S:15][CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])=[CH:21][CH:20]=3)[N:18]=2)=[O:7])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

참가 물질

6

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 7063853N-[4-(2-amino-4-thiazolyl)phenyl]MethanesulfonamideHCID 20540373N-isopropyl-3,3-diphenylpropan-1-amine

생성물 1

HCID 251744811-(3,3-Diphenylpropyl)-1-isopropyl-3-(4-(4-(methylsulfonamido)phenyl)thiazol-2-yl)urea수율 60.4%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매

실험 절차

To a solution of CDI (0.163 g, 1.01 mmol) and DMAP (0.129 g, 1.06 mmol) in DMF (1 mL) at room temperature was added N-(4-(2-aminothiazol-4-yl)phenyl)methanesulfonamide 5 (0.178 g, 0.661 mmol). The reaction mixture was stirred at room temperature for 40 h and N-isopropyl-3,3-diphenylpropan-1-amine 2 (0.215 g, 0.849 mmol) was added. The reaction mixture was stirred at room temperature for 8 h and heated to 40° C. for 15 h. Direct purification by flash column chromatography on silica gel (eluted with 10% to 50% EtOAc in DCM) followed by purification by flash column chromatography on silica gel (eluted with 30% to 80% EtOAc in hexanes) gave 1-(3,3-diphenylpropyl)-1-isopropyl-3-(4-(4-(methylsulfonamido)-phenyl)thiazol-2-yl)urea 6 (0.219 g, 60.4% yield) as a white solid.

후처리

  1. stirringThe reaction mixture was stirred at room temperature for 8 h
  2. temperatureheated to 40° C. for 15 h
  3. customDirect purification by flash column chromatography on silica gel (eluted with 10% to 50% EtOAc in DCM)
  4. customfollowed by purification by flash column chromatography on silica gel (eluted with 30% to 80% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-cb46160e71a74911ae96806a71682245
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324396B2

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