N-(5-Chloro-2-methoxyphenyl)thiourea → N-(2-(5-Chloro-2-methoxyphenylamino)-4,5'-bithiazol-2'-yl)pivalamide

HRID 1942995노트

반응식

HRID 1942995 반응식
Br[CH2:2][C:3]([C:5]1[S:9][C:8]([NH:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[N:7][CH:6]=1)=O.[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([O:28][CH3:29])=[C:22]([NH:24][C:25]([NH2:27])=[S:26])[CH:23]=1>CCO>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([O:28][CH3:29])=[C:22]([NH:24][C:25]2[S:26][CH:2]=[C:3]([C:5]3[S:9][C:8]([NH:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[N:7][CH:6]=3)[N:27]=2)[CH:23]=1

참가 물질

4

반응물 2

HCID 2732660N-(5-Chloro-2-methoxyphenyl)thioureaHCID 25130826N-(5-(2-Bromoacetyl)thiazol-2-yl)pivalamide

생성물 1

HCID 25130491N-(2-(5-Chloro-2-methoxyphenylamino)-4,5'-bithiazol-2'-yl)pivalamide수율 84%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A suspension of 21z (0.73 g, 2.3 mmol) and N-(5-chloro-2-methoxyphenyl)thiourea (0.73 g, 2.53 mmol) in EtOH (25 mL) was refuxed for 30 min. Upon cooling, the product was collected by filtration and washed with cold ethanol to yield 22z as a pale yellow solid (0.40 g, 84%). Mp decomposition at 216° C. 1H NMR (600 MHz, DMSO-d6): δ 11.86 (br s, 1H) 9.93 (br s, 1H), 8.64 (d, J=2.4 Hz, 1H), 7.83 (s, 1H), 7.18 (s, 1H), 7.02 (d, J=8.4 Hz, 1H), 6.98 (dd, J=8.4 Hz, 2.4 Hz, 1H), 3.86 (s, 3H), 1.25 (s, 9H). 13C NMR (150 MHz, DMSO-d6): δ 176.7, 162.1, 158.9, 146.6, 140.2, 136.4, 130.5, 124.7, 124.2, 121.3, 117.3, 112.1, 91.0, 56.1, 38.8, 26.6. HRMS m/z (ESI) calcd. for C18H19ClN4O2S2 (M+H)+ 423.0711. Found 423.0713.

후처리

  1. temperatureUpon cooling
  2. filtrationthe product was collected by filtration
  3. washwashed with cold ethanol

출처 및 근거

ORD 기록
ord-13875481471948a38197ae3ab5b2e260
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389736B2

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