Triethylamine → HCID 58266751, compound

HRID 1505838Notes

Reaction equation

HRID 1505838 reaction equation
[Br:1][C:2]1[CH:17]=[N:16][C:5]2[NH:6][C:7]3[CH:12]=[N:11][C:10]([C:13]([NH2:15])=O)=[CH:9][C:8]=3[C:4]=2[CH:3]=1.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C1COCC1>[Br:1][C:2]1[CH:17]=[N:16][C:5]2[NH:6][C:7]3[CH:12]=[N:11][C:10]([C:13]#[N:15])=[CH:9][C:8]=3[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 582667993-Bromo-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carboxylic acid amide

Product 1

HCID 58266751HCID 58266751, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled solution (0° C.) of a mixture of 3-bromo-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carboxylic acid amide (5.0 g, 17.2 mmol) and triethylamine (24.0 mL, 172 mmol) in THF (200 mL) was slowly added trifluoroacetic anhydride (12.0 mL, 86 mmol). Upon complete addition, the reaction mixture was allowed to warm to ambient temperature and the stirring was continued for an additional 4 h. After this time, the solvent was removed in vacuo and the resultant residue was loaded onto H-MN. The residue was then purified by flash chromatography (silica, 330 g column, ISCO, 0-100% ethyl acetate in hexane) to afford the title compound as a pale brown solid (2.30 g, 49%). 1H NMR (DMSO-D6, 300 MHz): 13.05 (s, 1H), 9.08-9.04 (m, 2H), 8.91 (d, J=1.1 Hz, 1H), 8.79 (d, J=2.3 Hz, 1H). LCMS (Method B): RT=2.98 min, M+H+=271, 273.

Workup

  1. additionUpon complete addition
  2. customAfter this time, the solvent was removed in vacuo
  3. customThe residue was then purified by flash chromatography (silica, 330 g column, ISCO, 0-100% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-67bca9f36b48441bbc2bb89bc13b6a77
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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