Water → 2-Chloro-N-[4-chloro-6-(4-chlorophenylamino)-pyrimidin-5-yl]-benzamide

HRID 1246782

반응식

HRID 1246782 반응식
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[C:3]=1[NH2:16].[Cl:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21].O>CN(C)C(=O)C>[Cl:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([NH:16][C:3]1[C:2]([Cl:1])=[N:7][CH:6]=[N:5][C:4]=1[NH:8][C:9]1[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=1)=[O:21]

참가 물질

5

반응물 3

HCID 962WaterHCID 691102-Chlorobenzoyl chlorideHCID 167263116-Chloro-N4-(4-chlorophenyl)pyrimidine-4,5-diamine

생성물 1

HCID 167263122-Chloro-N-[4-chloro-6-(4-chlorophenylamino)-pyrimidin-5-yl]-benzamide수율 82%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

반응 조건

온도
5 °C

실험 절차

6-Chloro-N4-(4-chlorophenyl)-pyrimidine-4,5-diamine I-(1A-1)a (1.00 g, 3.92 mmol) was dissolved in 6 ml of N,N-dimethylacetamide giving a clear brown solution. After cooling to 5° C., neat 2-chlorobenzoyl chloride (0.80 g, 4.34 mmol) was added over 1 minute. The solution was warmed to room temperature and stirred for 4 hours. Addition of water (15 ml) caused white precipitate to come out of solution. The mixture was stirred for an additional 30 minutes at room temperature, then the precipitate was collected by vacuum filtration, rinsing with H2O and then hexanes. The solid was further dried under vacuum to give I-(4A-7)a as a colorless solid (1.27 g, 82%): +ACPI MS (M+1) 393.1; 1H NMR (400 MHz, DMSO-d6) δ 10.02 (s, 1H), 9.11 (s, 1H), 8.40 (s, 1H), 7.93 (dd, J=7.4, 1.6 Hz, 1H), 7.66–7.40 (m, 7H).

후처리

  1. temperatureThe solution was warmed to room temperature
  2. stirringThe mixture was stirred for an additional 30 minutes at room temperature
  3. filtrationthe precipitate was collected by vacuum filtration
  4. washrinsing with H2O
  5. customThe solid was further dried under vacuum

출처 및 근거

ORD 기록
ord-08f07784aef941d5ba0e1c817d2762cd
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07129239B2

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