Ethyl orthoformate → HCID 57500681, compound

HRID 1919660Notes

Reaction equation

HRID 1919660 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][C:21]([C:23]([NH:25][NH2:26])=[O:24])=[CH:22][C:11]=3[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH:27](OCC)(OCC)OCC>>[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][C:21]([C:23]4[O:24][CH:27]=[N:26][N:25]=4)=[CH:22][C:11]=3[N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 57500680HCID 57500680, compound

Product 1

HCID 57500681HCID 57500681, compoundYield 56%

Procedure

5-(3-chlorophenylamino)benzo[c][2,6]naphthyridine-8-carbohydrazide (1.0 eq, 21 mg, 0.057 mmol) was suspended in triethyl orthoformate (0.5 ml) and the mixture reacted in a microwave reactor at 120° C. for 80 minutes. The precipitate that formed upon cooling was filtered and dried to afford N-(3-chlorophenyl)-8-(1,3,4-oxadiazol-2-yl)benzo[c][2,6]naphthyridin-5-amine as a solid (12 mg, 56% yield). LCMS (ES): 95% pure, m/z 374 [M+1]+.

Workup

  1. customthe mixture reacted in a microwave reactor at 120° C. for 80 minutes
  2. customThe precipitate that formed
  3. temperatureupon cooling
  4. filtrationwas filtered
  5. customdried

Sources & evidence

ORD record
ord-b6e5f1cbd8f84422b3e52ec99fcf7c2c
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

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