Tert-Butylamine → 3-Nitroquinolin-4-amine

HRID 419285

反応式

HRID 419285 の反応式
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]

参加物

5

反応物 3

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

生成物 2

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

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-32557b9269804b7fa735a49fb7ca7358
出典データセット
uspto-grants-2012_01
特許番号
US08093390B2

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