Dicyclohexylcarbodiimide → HCID 71515463, 화합물

HRID 1855213노트

반응식

HRID 1855213 반응식
[Cl:1][CH2:2][CH2:3][N:4]([CH2:15][CH2:16][Cl:17])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=O)=[CH:7][CH:6]=1.C1CCC(N=C=NC2CCCCC2)CC1.[C:33]([C:37]1[O:41][C:40]([CH2:42][S:43][C:44]2[S:48][C:47]([NH2:49])=[N:46][CH:45]=2)=[N:39][CH:38]=1)([CH3:36])([CH3:35])[CH3:34]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:17][CH2:16][CH2:15][N:4]([CH2:3][CH2:2][Cl:1])[C:5]1[CH:6]=[CH:7][C:8]([CH2:11][C:12]([NH:49][C:47]2[S:48][C:44]([S:43][CH2:42][C:40]3[O:41][C:37]([C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:38][N:39]=3)=[CH:45][N:46]=2)=[O:14])=[CH:9][CH:10]=1

참가 물질

6

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 25306PhenacidHCID 110654845-(((5-(tert-Butyl)oxazol-2-yl)methyl)thio)thiazol-2-amine

생성물 1

HCID 71515463HCID 71515463, 화합물수율 76%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

To a stirred methylene chloride solution (20 ml) was added DMAP (438 mg, 3.59 mmol) and 2-(4-(bis(2-chloroethyl)amino)phenyl)acetic acid (B-5) (906 mg, 3.27 mmol). Subsequently, DCC (690 mg, 3.35 mmol) was added to reaction mixture, followed by addition of 5-((5-tert-butyloxazol-2-yl)methylthio)thiazol-2-amine (Intermediate CY-200) (800 mg, 2.97 mmol). The mixture was stirred at r.t for 24 h. After removing dicyclohexylurea (DCU) by filtration, the filtrate was concentrated in vacuum and dried over Na2SO4. The residue was purified by silica gel chromatography eluting with CH2Cl2: EtOAc=20:1 to afford total product (1.2 g, 76%) as a gray solid. LC-MS: (M+H)+=528. 1H NMR (300 MHz, CDCl3) δ 10.17 (s, 1H), 7.28-7.30 (m, 1H), 7.17 (d, J=8.4 Hz, 2H), 6.69 (d, J=8.7 Hz, 2H), 6.58 (s, 1H), 3.95 (s, 2H), 363-3.79 (m, 10H), 1.26 (s, 9H).

후처리

  1. customAfter removing dicyclohexylurea (DCU)
  2. filtrationby filtration
  3. concentrationthe filtrate was concentrated in vacuum
  4. dry with materialdried over Na2SO4
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with CH2Cl2

출처 및 근거

ORD 기록
ord-d7b30cf313d545548dbd3ad41ef646d1
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962855B2

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