Tert-Butylamine → 3-Nitroquinolin-4-amine

HRID 419285

반응식

HRID 419285 반응식
C(O[C:9]1[C:18]([N+:19]([O-:21])=[O:20])=[C:17](Cl)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1)C1C=CC=CC=1.C(O[C:31]1[C:40]([N+:41]([O-:43])=[O:42])=[C:39](Cl)[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][N:37]=2)[N:32]=1)C1C=CC=CC=1.C([NH2:49])(C)(C)C>>[N+:19]([C:18]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[NH2:32])=[CH:15][CH:14]=[CH:13][CH:12]=2)([O-:21])=[O:20].[N+:41]([C:40]1[CH:31]=[N:32][C:33]2[C:38]([C:39]=1[NH2:49])=[N:37][CH:36]=[CH:35][CH:34]=2)([O-:43])=[O:42]

참가 물질

5

반응물 3

HCID 6385Tert-ButylamineHCID 21075762Benzyloxy-4-chloro-3-nitroquinolineHCID 66650176Benzyloxy-4-chloro-3-nitro[1,5]naphthyridine

생성물 2

HCID 2800053-Nitroquinolin-4-amineHCID 131227883-Nitro-1,5-naphthyridin-4-amine

실험 절차

Compounds of the invention can also be prepared according to Reaction Scheme V, wherein Bn, E, R, R3-1, and n are as defined above; P is an amino protecting group; and Da is —(CH2)1-4—. In step (1) of Reaction Scheme V, a benzyloxy-4-chloro-3-nitroquinoline or benzyloxy-4-chloro-3-nitro[1,5]naphthyridine of Formula XLI is reacted with tert-butylamine in the presence of base, and the tert-butyl group is subsequently removed under acidic conditions to provide a 3-nitroquinolin-4-amine or 3-nitro[1,5]naphthyridin-4-amine of Formula XLII, which is reduced in step (2) to provide a quinoline-3,4-diamine or [1,5]naphthyridine-3,4-diamine of Formula XLIII. In step (3) of Reaction Scheme V, a. quinoline-3,4-diamine or [1,5]naphthyridine-3,4-diamine of Formula XLIII is reacted with acetic acid or acetyl chloride to provide a 2-methyl-1H-imidazo[4,5-c]quinoline or a 2-methyl-1H-imidazo[4,5-c][1,5]naphthyridine of Formula XLIV, which undergoes protection at the 1-position in step (4) with a suitable protecting group. In step (5) of Reaction Scheme V, the 2-methyl group of a 1H-imidazo[4,5-c]quinoline or 1H-imidazo[4,5-c][1,5]naphthyridine of Formula XLV is deprotonated with n-butyllithium and subsequently reacted with an alkylating agent of formula Br—CH2-Da-CH2—Cl, and the product of Formula XLVI is then deprotected using conventional methods to provide a 1H-imidazo[4,5-c]quinoline or 1H-imidazo[4,5-c][1,5]naphthyridine of Formula XLVII. The compound of Formula XLVII is then cyclized to provide a compound of Formula XLVIII. Steps (1) through (7) of Reaction Scheme V can be carried out using the conditions described in U.S. Pat. No. 5,482,936 (Lindstrom).

후처리

  1. customCompounds of the invention can also be prepared
  2. customaccording to Reaction Scheme V, wherein Bn, E, R, R3-1, and n
  3. customIn step (1) of Reaction Scheme V
  4. customthe tert-butyl group is subsequently removed under acidic conditions

출처 및 근거

ORD 기록
ord-32557b9269804b7fa735a49fb7ca7358
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093390B2

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