Sulfuric Acid → HCID 57561027, compound

HRID 1724844Notes

Reaction equation

HRID 1724844 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]1[C:4]([C:9]2[N:18]=[C:17]3[C:12]([C:13]([NH:21][C:22]4[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][N:23]=4)=[CH:14][C:15]([C:19]#[N:20])=[N:16]3)=[CH:11][CH:10]=2)=[N:5][CH:6]=[CH:7][CH:8]=1.[OH:34]S(O)(=O)=O>>[F:33][C:2]([F:1])([F:32])[C:3]1[C:4]([C:9]2[N:18]=[C:17]3[C:12]([C:13]([NH:21][C:22]4[CH:27]=[CH:26][C:25]([C:28]([F:29])([F:30])[F:31])=[CH:24][N:23]=4)=[CH:14][C:15]([C:19]([NH2:20])=[O:34])=[N:16]3)=[CH:11][CH:10]=2)=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 57561029HCID 57561029, compound

Product 1

HCID 57561027HCID 57561027, compound

Procedure

Dissolve 7-[3-(trifluoromethyl)pyridin-2-yl]-4-{[5-(trifluoromethyl)pyridin-2-yl]amino}-1,8-naphthyridine-2-carbonitrile (25 mg, 0.054 mmol) in concentrated H2SO4 (2 mL) and stir the mixture overnight at ambient temperature. Pour the mixture onto ice and adjust the pH to about 7-8. Filter off the resulting precipitate to yield the title compound as an off-white solid. MS 479.02 (M+1). 1H NMR δ (CD3OD) 9.32 (1H, s), 9.10 (1H, d), 8.97 (1H, d), 8.71 (1H, s), 8.41 (1H, d), 8.05 (1H, d), 7.95 (1H, d), 7.82 (1H, m), 8.90 (1H,s), 7.44.

Workup

  1. additionPour the mixture onto ice
  2. filtrationFilter off the resulting precipitate

Sources & evidence

ORD record
ord-e2d512dc2a94443a96833d14ba7912c9
Source dataset
uspto-grants-2009_02
Patent number
US07488740B2

Reaction notes

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