Hydrochloric Acid → 4-{[4-Chloro-3-(trifluoromethyl)benzyl]amino}-6-nitroquinazoline-8-carboxylic acid

HRID 474407

반응식

HRID 474407 반응식
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][NH:7][C:8]2[C:17]3[C:12](=[C:13]([C:21]([O:23]C)=[O:22])[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=3)[N:11]=[CH:10][N:9]=2)=[CH:4][C:3]=1[C:27]([F:30])([F:29])[F:28].C1COCC1.[Li+].[OH-].Cl>O>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][NH:7][C:8]2[C:17]3[C:12](=[C:13]([C:21]([OH:23])=[O:22])[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=3)[N:11]=[CH:10][N:9]=2)=[CH:4][C:3]=1[C:27]([F:30])([F:28])[F:29]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 66763565Methyl 4-{[4-chloro-3-(trifluoromethyl)benzyl]amino}-6-nitroquinazoline-8-carboxylate

생성물 1

HCID 667636364-{[4-Chloro-3-(trifluoromethyl)benzyl]amino}-6-nitroquinazoline-8-carboxylic acid수율 97%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Methyl 4-{[4-chloro-3-(trifluoromethyl)benzyl]amino}-6-nitroquinazoline-8-carboxylate (190 mg, 0.43 mmol) was treated with a mixture of 650 μL of THF and 650 μL of 2N LiOH (1.3 mmol, 3 equiv.)) at rt for 2 h. Water was added and pH was adjusted to ˜4 with 2N HCl. The precipitate was collected as the desired acid by filtration, and washing with water in 97% yield. 1HNMR (in DMSO): 4.95 (s, 2H), 7.69-7.74 (m, 2H), 7.94 (d, J=1.4 Hz, 1H), 8.81 (s, 1H), 9.02 (d, J=2.2 Hz, 1H), 9.62 (d, J=2.5 Hz, 1H). Mass: M+H+: 427.

후처리

  1. filtrationThe precipitate was collected as the desired acid by filtration
  2. washwashing with water in 97% yield

출처 및 근거

ORD 기록
ord-74fa58a5c9cc4735b76f20a0383d378d
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637532B2

연결된 노트

불러오는 중…