1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 90408866、化合物

HRID 510221ノート

反応式

HRID 510221 の反応式
[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

参加物

8

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 27366772-Chloro-3-(trifluoromethyl)benzoic acidHCID 90408866HCID 90408866、化合物

生成物 2

HCID 90407553HCID 90407553、化合物収率 24%HCID 90408866HCID 90408866、化合物収率 39%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

出典と根拠

ORDレコード
ord-400618ce05d04a238c40fd347dc6d2a1
出典データセット
uspto-grants-2015_08
特許番号
US09096596B2

反応ノート

読み込み中…