{3-[(Ethanesulfonyl)amino]phenyl}boronic acid → Ethanesulfonic acid [3-(1-chloro-10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-phenyl]-amide

HRID 2218703

반응식

HRID 2218703 반응식
Br[CH:2]=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[C:13]([Cl:14])[C:8]=2[CH2:7][CH2:6][C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]1=2.[CH2:19]([S:21]([NH:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1)(=[O:23])=[O:22])[CH3:20]>>[Cl:14][C:13]1[C:8]2[CH2:7][CH2:6][C:5]3[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=3[C:3](=[CH:2][C:29]3[CH:30]=[C:25]([NH:24][S:21]([CH2:19][CH3:20])(=[O:22])=[O:23])[CH:26]=[CH:27][CH:28]=3)[C:9]=2[CH:10]=[CH:11][CH:12]=1

참가 물질

3

반응물 2

HCID 46738824{3-[(Ethanesulfonyl)amino]phenyl}boronic acidHCID 688913895-bromomethylene-1-chloro-10,11dihydro-5H-dibenzo[a,d]cycloheptene

생성물 1

HCID 72556991Ethanesulfonic acid [3-(1-chloro-10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-phenyl]-amide

실험 절차

Following procedures essentially as described in Example 219, below, and using 5-bromomethylene-1-chloro-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (100 mg, 0.313 mmol) and 3-ethanesulfonylaminophenylboronic acid (79 mg, 0.344 mmol), affords 112 mg (84%) of a mixture of geometric isomers of the title compound (Example 208(a)) as a yellow solid (MS (ES) 424 (M+H); HPLC shows 94% purity). Separate geometric isomers using a chromatatron rotor (10% ethyl acetate/hexanes) to afford 13 mg (10%) of the Z-isomer (Example 208(b)) of the title compound as a white solid, (MS (ES) 424 (M+H), 422 (M−H). HPLC shows 96% purity). Continue to elute and isolate 6 mg (5%) of the E-isomer (Example 208(c))of the title compound as a white solid (MS (ES) 424 (M+H), 422 (M−H); HPLC shows 97% purity).

출처 및 근거

ORD 기록
ord-d5218a5ad835459f980f233ca04aeba8
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07411072B2

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