Thioglycolic Acid → N-Cyclopropyl-3-(2-mercaptoacetamido)-4-methylbenzamide

HRID 1951272노트

반응식

HRID 1951272 반응식
[SH:1][CH2:2][C:3]([OH:5])=O.Cl.[NH2:7][C:8]1[CH:9]=[C:10]([CH:17]=[CH:18][C:19]=1[CH3:20])[C:11]([NH:13][CH:14]1[CH2:16][CH2:15]1)=[O:12]>C1(C)C=CC=CC=1>[CH:14]1([NH:13][C:11](=[O:12])[C:10]2[CH:17]=[CH:18][C:19]([CH3:20])=[C:8]([NH:7][C:3](=[O:5])[CH2:2][SH:1])[CH:9]=2)[CH2:15][CH2:16]1

참가 물질

4

반응물 2

HCID 1133Thioglycolic Acid2회HCID 442031943-Amino-N-cyclopropyl-4-methylbenzamide hydrochloride

생성물 1

HCID 59761419N-Cyclopropyl-3-(2-mercaptoacetamido)-4-methylbenzamide수율 32%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A solution of mercaptoacetic acid (1.65 mL, 24.2 mmol) and 5.0 g (22 mmol) of 3-amino-N-cyclopropyl-4-methylbenzamide hydrochloride (prepared as described in WO 04/071440) in toluene (40 mL) was refluxed for 16 h. At this time, an additional 0.8 mL of mercaptoacetic acid was added and the mixture was continued at reflux for an additional 2 days. After cooling to rt, the solid was collected by vacuum filtration and was rinsed with EtOAc (2×50 mL). The resulting solid was then slurried in water (50 mL) and the solid was recollected by vacuum filtration and rinsed with add'n water. The resulting solid was air dried in the funnel then under vacuum overnight to afford 1.86 g (32%) of a white solid as compound a. HPLC Ret time=1.83 min. LCMS [M+H]+ 265.37.

후처리

  1. temperatureat reflux for an additional 2 days
  2. filtrationthe solid was collected by vacuum filtration
  3. washwas rinsed with EtOAc (2×50 mL)
  4. filtrationthe solid was recollected by vacuum filtration
  5. washrinsed with add'n water
  6. customdried in the funnel

출처 및 근거

ORD 기록
ord-d45f80d89f994a5fa9d26640c0f83629
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08404689B2

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