Methyl chloroformate → (S)-methyl (4-(5-(3-cyano-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-2,3-dihydro-1H-inden-1-yl)carbamate

HRID 1891467노트

반응식

HRID 1891467 반응식
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.Cl[C:30]([O:32][CH3:33])=[O:31]>C(Cl)Cl>[CH3:33][O:32][C:30](=[O:31])[NH: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]([C:22]#[N:23])[CH:24]=4)=[N:14][N:13]=3)[CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4]1

참가 물질

4

반응물 2

HCID 6586Methyl chloroformateHCID 67193845(S)-5-(5-(1-amino-2,3-dihydro-1H-inden-4-yl)-1,3,4-thiadiazol-2-yl)-2-isopropoxybenzonitrile hydrochloride

생성물 1

HCID 53233873(S)-methyl (4-(5-(3-cyano-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-2,3-dihydro-1H-inden-1-yl)carbamate수율 92.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Prepared using General Procedure 8. 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 (15 mg, 0.03 mmol) and TEA (11 mg, 0.1 mmol) in DCM (1 mL) was added methyl chloroformate (10 mg, 0.1). The reaction mixture was stirred at room temperature for 16 h. The solvent was evaporated and water (2 mL) was added. The resulting solid was filtered, washed with water, and dried under high vacuum to afford 12 mg (92%) of (S)-methyl(4-(5-(3-cyano-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-2,3-dihydro-1H-inden-1-yl)carbamate 16 as white solid. LCMS-ESI (m/z) calculated for C23H22N4O3S: 434.1; found 435.3 [M+H]+, tR=3.69 min.

후처리

  1. customPrepared
  2. customThe solvent was evaporated
  3. additionwater (2 mL) was added
  4. filtrationThe resulting solid was filtered
  5. washwashed with water
  6. customdried under high vacuum

출처 및 근거

ORD 기록
ord-32187bbbb9e94db7a7459ccd28078655
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507538B2

반응 노트

불러오는 중…