1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 90408866, 화합물

HRID 510221노트

반응식

HRID 510221 반응식
[Cl:1][C:2]1[C:3]2[CH2:11][CH2:10][N:9]([C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[C:15]=3[Cl:24])=[O:13])[CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1.ClC1C(C(F)(F)F)=CC=CC=1C(O)=O.CCN=C=NCCCN(C)C.[CH:50]1[CH:51]=[CH:52][C:53]2[N:58]([OH:59])[N:57]=[N:56][C:54]=2[CH:55]=1>C(Cl)Cl.CCOC(C)=O>[Cl:1][C:2]1[C:3]2[CH2:11][CH2:10][N:9]([C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:21])[F:22])[C:15]=3[Cl:24])=[O:13])[CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1.[N:58]1([O:59][C:2]2[C:3]3[CH2:11][CH2:10][N:9]([C:12]([C:14]4[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[C:15]=4[Cl:24])=[O:13])[CH2:8][C:4]=3[N:5]=[CH:6][N:7]=2)[C:53]2[CH:52]=[CH:51][CH:50]=[CH:55][C:54]=2[N:56]=[N:57]1

참가 물질

8

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 27366772-Chloro-3-(trifluoromethyl)benzoic acidHCID 90408866HCID 90408866, 화합물

생성물 2

HCID 904075534-(1H-benzotriazol-1-yloxy)-7-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine수율 24%HCID 90408866HCID 90408866, 화합물수율 39%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of the product of Intermediate 3 step a (305 mg, 1.80 mmol) in DCM (9 mL) was added 2-chloro-3-(trifluoromethyl)benzoic acid (404 mg, 1.80 mmol) followed by EDCI (517 mg, 2.70 mmol), HOBt (170 mg, 1.26 mmol) and TEA (0.50 mL, 3.60 mmol). The mixture was stirred overnight and then loaded directly on a column. Chromatography on SiO2 eluting with EtOAc/Hex afforded the desired product (267 mg, 39%) and 4-(1H-benzotriazol-1-yloxy)-7-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine (203 mg, 24%) as a side product. MS (ESI) mass calcd. C15H10Cl2F3N3O, 375.02. m/z found 376.0 [M+H]+. 1H NMR (500 MHz, CDCl3): 8.89-8.74 (m, 1H), 7.84-7.76 (m, 1H), 7.55-7.45 (m, 2H), 5.13-4.94 (m, 1H), 4.54-4.35 (m, 1H), 4.23-4.06 (m, 1H), 3.64-3.52 (m, 1H), 3.10-2.78 (m, 2H).

출처 및 근거

ORD 기록
ord-400618ce05d04a238c40fd347dc6d2a1
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096596B2

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