1,1,1-Trimethoxybutane → 1-{[3-(4-Fluorophenyl)isoxazol-5-yl]methyl}-2-propyl-1H-imidazo[4,5-c][1,5]naphthyridine

HRID 606081Notes

Reaction equation

HRID 606081 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([CH2:13][NH:14][C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][N:23]=4)[N:18]=[CH:17][C:16]=3[NH2:25])[O:10][N:9]=2)=[CH:4][CH:3]=1.[C:26](OC)(OC)(OC)[CH2:27][CH2:28][CH3:29]>Cl.N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:12]=[C:11]([CH2:13][N:14]3[C:15]4[C:24]5[N:23]=[CH:22][CH:21]=[CH:20][C:19]=5[N:18]=[CH:17][C:16]=4[N:25]=[C:26]3[CH2:27][CH2:28][CH3:29])[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1235121,1,1-TrimethoxybutaneHCID 86616886N4-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}[1,5]naphthyridine-3,4-diamine

Product 1

HCID 670413321-{[3-(4-Fluorophenyl)isoxazol-5-yl]methyl}-2-propyl-1H-imidazo[4,5-c][1,5]naphthyridineYield 35.7%

Reagents, catalysts & solvents 1

HCID 10176127Pyridinium chlorideCatalyst

Procedure

The methods described in Part A of Example 13 were used to treat N4-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}[1,5]naphthyridine-3,4-diamine (2.6 g, 7.8 mmol) with trimethyl orthobutyrate (1.9 mL, 12 mmol) in the presence of pyridine hydrochloride (0.018 g, 0.16 mmol) and isolated and purify the final product with the modification that the silica column was eluting with 60-90% ethyl acetate in dichloromethane. 1-{[3-(4-Fluorophenyl)isoxazol-5-yl]methyl}-2-propyl-1H-imidazo[4,5-c][1,5]naphthyridine (1.08 g) was obtained as a white solid.

Workup

  1. customisolated
  2. custompurify the final product with the modification that the silica column
  3. washwas eluting with 60-90% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-79b1634470ad41c19f24492e0ec250ab
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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