Dimethylamine, hydrochloride → HCID 11432721, compound

HRID 13850Notes

Reaction equation

HRID 13850 reaction equation
Cl.[CH3:2][NH:3][CH3:4].[Al](C)(C)C.[C:9]([NH:12][C:13]1[C:22]2[C:17](=[N:18][C:19]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=3[Cl:37])=[C:20]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)[CH:21]=2)[N:16]([CH3:38])[C:15](=[O:39])[C:14]=1[C:40](OC)=[O:41])(=[O:11])[CH3:10]>C1(C)C=CC=CC=1>[C:9]([NH:12][C:13]1[C:22]2[C:17](=[N:18][C:19]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=3[Cl:37])=[C:20]([C:23]3[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=3)[CH:21]=2)[N:16]([CH3:38])[C:15](=[O:39])[C:14]=1[C:40]([N:3]([CH3:4])[CH3:2])=[O:41])(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 11307094Methyl 4-(acetylamino)-6(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylateHCID 16682925Trimethylaluminum

Product 1

HCID 11432721HCID 11432721, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To dimethylamine hydrochloride (26.1 mg) in toluene (2 mL) was added Al(CH3)3 (0.16 mL) at 0° C. The reaction stirred for about 30 minutes before adding the product of EXAMPLE 91 (85 mg) in toluene (1 mL). The reaction stirred for 3.5 hours at 50° C. and was quenched with aqueous 1 M HCl. The reaction was diluted with EtOAc washed with aqueous 1 M HCl. The solution was dried (Na2SO4) and concentrated. The concentrated residue was purified by preparative TLC on silica gel eluted with 6% methanol in CH2Cl2 affording the title compound. HPLC/MS: 543.0 (M+1), 545.0 (M+3); Rt=3.51 min.

Workup

  1. stirringThe reaction stirred for 3.5 hours at 50° C.
  2. customwas quenched with aqueous 1 M HCl
  3. additionThe reaction was diluted with EtOAc
  4. washwashed with aqueous 1 M HCl
  5. dry with materialThe solution was dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe concentrated residue was purified by preparative TLC on silica gel
  8. washeluted with 6% methanol in CH2Cl2 affording the title compound

Sources & evidence

ORD record
ord-c28aed103c1d4bb9b51add5a63dc8396
Source dataset
uspto-grants-2010_06
Patent number
US07728141B2

Reaction notes

Loading…