Acetyl chloride → HCID 178432311, compound

HRID 419286Notes

Reaction equation

HRID 419286 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([NH2:11])=[C:3]([NH2:12])[CH:2]=1.N1C2C(=NC=CC=2)C(N)=[C:15](N)[CH:14]=1.C(Cl)(=O)C>C(O)(=O)C>[CH3:14][C:15]1[NH:11][C:4]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=3[N:1]=[CH:2][C:3]=2[N:12]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 15142893,4-DiaminoquinolineHCID 22172703[1,5]Naphthyridine-3,4-diamine

Product 1

HCID 178432311HCID 178432311, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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).

Workup

  1. customIn step (3) of Reaction Scheme V

Sources & evidence

ORD record
ord-d54b901fcac840349d5e5f8ab81d4e44
Source dataset
uspto-grants-2012_01
Patent number
US08093390B2

Reaction notes

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