Hydrochloric Acid → HCID 57636160, 화합물

HRID 1432202

반응식

HRID 1432202 반응식
[CH3:1][C:2]1[CH:11]=[C:10]([NH2:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH2:13])[CH:8]=2)[N:3]=1.[Cl:14][C:15]1[N:20]=[C:19](Cl)[CH:18]=[C:17]([CH3:22])[N:16]=1.Cl>C(O)CO.O>[Cl:14][C:15]1[N:20]=[C:19]([NH:13][C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[N:3]=[C:2]([CH3:1])[CH:11]=[C:10]3[NH2:12])[CH:18]=[C:17]([CH3:22])[N:16]=1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 794712,4-Dichloro-6-methylpyrimidineHCID 2239952-Methylquinoline-4,6-diamine

생성물 1

HCID 57636160HCID 57636160, 화합물수율 27%

시약·촉매·용매 2

HCID 174Ethylene Glycol용매HCID 962Water용매

실험 절차

Diaminoquinoline 7 (72.0 g, 0.416 mol) and 2,4-dichloro-6-methylpyrimidine (8) (67.8 g, 0.416 mol) were suspended in ethylene glycol (1 L). Addition of 37% HCl (35 mL, 0.43 mol) resulted in a yellow solution which was heated to and held at 50° C. for 4.5 h. The mixture was diluted with chilled water (1 L) which resulted in a thick white paste-like precipitate and the mixture was filtered through Celite. The Celite and solid containing the product and bis-substituted by-product was slurried in water (4 L) and the Celite and insoluble by-product were removed by filtration. The filtrate pH was adjusted to 14 using 1N aqueous NaOH (1 L) resulting in precipitation of product which was removed by filtration. The damp product was transferred to a rotovap flask and dried in vacuo by azeotropic water removal with toluene (3×1.5 L). Product 9 was obtained as an off-white solid (33.4 g, 27% yield; Notebook reference A134-137). Another batch of 9 (7.4 g, 17% yield; Notebook reference A134-134) was similarly obtained by reaction of 7 (25.0 g, 0.144 mol) and recovery as above; MS [M+1]=300, 302; 13C NMR (DMSO) δ 167.51, 162.58, 159.22, 157.61, 151.05, 145.99, 133.17, 128.96, 125.39, 117.38, 114.23, 102.45, 102.26, 24.68, 23.19.

후처리

  1. customresulted in a yellow solution which
  2. temperaturewas heated to and
  3. customresulted in a thick white paste-like precipitate
  4. filtrationthe mixture was filtered through Celite
  5. additionThe Celite and solid containing the product and bis-substituted by-product
  6. customthe Celite and insoluble by-product were removed by filtration
  7. customresulting in precipitation of product which
  8. customwas removed by filtration
  9. customThe damp product was transferred to a rotovap flask
  10. dry with materialdried in vacuo by azeotropic water removal with toluene (3×1.5 L)

출처 및 근거

ORD 기록
ord-c03830271f61434c8f95e19948ae8e8c
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612080B2

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