Methylamine → 4-Chloro-6-methyl-2-(4-methyl-piperazin-1-yl)-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid

HRID 1927492노트

반응식

HRID 1927492 반응식
[CH3:1][NH2:2].C[O:4][C:5]([C:7]1[CH:8]=[C:9]([CH3:32])[C:10]2[O:16][C:15]3[C:17]([Cl:28])=[CH:18][C:19]([N:21]([CH2:25][CH2:26]Cl)[CH2:22][CH2:23]Cl)=[CH:20][C:14]=3[CH2:13][S:12](=[O:30])(=[O:29])[C:11]=2[CH:31]=1)=[O:6]>CO>[Cl:28][C:17]1[C:15]2[O:16][C:10]3[C:9]([CH3:32])=[CH:8][C:7]([C:5]([OH:4])=[O:6])=[CH:31][C:11]=3[S:12](=[O:29])(=[O:30])[CH2:13][C:14]=2[CH:20]=[C:19]([N:21]2[CH2:22][CH2:23][N:2]([CH3:1])[CH2:26][CH2:25]2)[CH:18]=1

참가 물질

4

반응물 2

HCID 6329MethylamineHCID 115260722-[Bis-(2-chloro-ethyl)-amino]-4-chloro-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

생성물 1

HCID 1317284754-Chloro-6-methyl-2-(4-methyl-piperazin-1-yl)-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Methanolic methylamine solution (20% v/v, 6 mL) was added to a solution of Example 102 (0.330 g, 0.69 mmol) in methanol (2 mL) in an atmosphere of nitrogen and sealed in a pressure reactor vessel at 100° C. for 6 h. It was brought to room temperature, flushed with N2 gas, treated with chilled water and dilute HCl to neutral pH. The solid that precipitated was filtered, washed with water, dried and purified using flash chromatography (silica gel, MeOH/CHCl3) to obtain the title compound as an off white solid. Yield: 0.260 g (86.37%). 1H NMR (DMSO-d6): δ 2.40 (s, 3H, CH3), 2.70 (s, 3H, CH3), 2.72-2.75 (m, 4H, 2CH2), 3.30-3.35 (m, 4H, 2CH2), 5.10 (s, 2H, CH2), 7.10 (s, 1H, Ar), 7.20 (s, 1H, Ar), 8.10 (s, 1H, Ar) and 8.25 (s, 1H, Ar); MS: m/e (ES+) 436 (M+1).

후처리

  1. customsealed in a pressure reactor vessel at 100° C. for 6 h
  2. customwas brought to room temperature
  3. customflushed with N2 gas
  4. additiontreated with chilled water and dilute HCl to neutral pH
  5. customThe solid that precipitated
  6. filtrationwas filtered
  7. washwashed with water
  8. customdried
  9. custompurified

출처 및 근거

ORD 기록
ord-f0ea493291a84ebcb9e00bca1285d7a3
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08183234B2

반응 노트

불러오는 중…