Ethyl orthoformate → N-(3-chlorophenyl)-7-(1,3,4-oxadiazol-2-yl)benzo[c][2,6]naphthyridin-5-amine

HRID 1919688Notes

Reaction equation

HRID 1919688 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][N:15]=[CH:16][CH:17]=3)[C:12]3=[CH:19][CH:20]=[CH:21][C:22]([C:23]([NH:25][NH2:26])=[O:24])=[C:11]3[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:27](OC(OCC)OCC)C>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][N:15]=[CH:16][CH:17]=3)[C:12]3[CH:19]=[CH:20][CH:21]=[C:22]([C:23]4[O:24][CH:27]=[N:26][N:25]=4)[C:11]=3[N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 575006985-(3-Chlorophenylamino)benzo[c][2,6]naphthyridine-7-carbohydrazide

Product 1

HCID 57393820N-(3-chlorophenyl)-7-(1,3,4-oxadiazol-2-yl)benzo[c][2,6]naphthyridin-5-amine

Procedure

5-(3-chlorophenylamino)benzo[c][2,6]naphthyridine-7-carbohydrazide (24 mg) was stirred in triethylorthoformate (1 ml) at 120° C. for 4 hours. The solid was filtered and triturated in CH2Cl2/MeOH. Impurities (mainly starting material) were removed by filtration and the filtrate containing the expecting compound was concentrated. The material was purified by preparative TLC on silica gel (5% methanol in CH2Cl2) to afford N-(3-chlorophenyl)-7-(1,3,4-oxadiazol-2-yl)benzo[c][2,6]naphthyridin-5-amine as a solid (8 mg). LCMS (ES): >95% pure, m/z 374 [M+1]+.

Workup

  1. filtrationThe solid was filtered
  2. customtriturated in CH2Cl2/MeOH
  3. customImpurities (mainly starting material) were removed by filtration
  4. additionthe filtrate containing the expecting compound
  5. concentrationwas concentrated
  6. customThe material was purified by preparative TLC on silica gel (5% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-9c42202d0f3a4542bd31f782310421f4
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

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