Methanesulfonyl chloride → (S)-N-(4-(5-(3-cyano-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-2,3-dihydro-1H-inden-1-yl)methanesulfonamide

HRID 1891477ノート

反応式

HRID 1891477 の反応式
Cl.[NH2:2][C@@H:3]1[C:11]2[C:6](=[C:7]([C:12]3[S:16][C:15]([C:17]4[CH:18]=[CH:19][C:20]([O:25][CH:26]([CH3:28])[CH3:27])=[C:21]([CH:24]=4)[C:22]#[N:23])=[N:14][N:13]=3)[CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4]1.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>C(Cl)Cl>[C:22]([C:21]1[CH:24]=[C:17]([C:15]2[S:16][C:12]([C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[C:6]=3[CH2:5][CH2:4][C@@H:3]4[NH:2][S:30]([CH3:29])(=[O:32])=[O:31])=[N:13][N:14]=2)[CH:18]=[CH:19][C:20]=1[O:25][CH:26]([CH3:28])[CH3:27])#[N:23]

参加物

4

反応物 2

HCID 31297Methanesulfonyl chlorideHCID 67193845(S)-5-(5-(1-amino-2,3-dihydro-1H-inden-4-yl)-1,3,4-thiadiazol-2-yl)-2-isopropoxybenzonitrile hydrochloride

生成物 1

HCID 53233329(S)-N-(4-(5-(3-cyano-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-2,3-dihydro-1H-inden-1-yl)methanesulfonamide収率 66%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Prepared using General Procedure 12. To a stirred solution of (S)-5-(5-(1-amino-2,3-dihydro-1H-inden-4-yl)-1,3,4-thiadiazol-2-yl)-2-isopropoxybenzonitrile hydrochloride 4 (20 mg, 0.04 mmol) and TEA (14.7 mg, 0.14 mmol) in DCM (2 mL) was added methane sulfonylchloride (8.3 mg, 0.07 mmol) and the mixture was stirred at room temperature for 16 h. The solvent was evaporated and the residue purified by preparative HPLC to afford 12 mg (55%) of (S)-N-(4-(5-(3-cyano-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-2,3-dihydro-1H-inden-1-yl)methanesulfonamide 33 as white solid. LCMS-ESI (m/z) calculated for C22H22N4O3S2: 454.1; found 455.1 [M+H]+, tR=3.48 min.

後処理

  1. customPrepared
  2. customThe solvent was evaporated
  3. customthe residue purified by preparative HPLC

出典と根拠

ORDレコード
ord-e1ca2f3aaaad49a9b7a08b387b1909b6
出典データセット
uspto-grants-2013_08
特許番号
US08507538B2

反応ノート

読み込み中…