Dimethylformamide → HCID 22767691, compound

HRID 1111736Notes

Reaction equation

HRID 1111736 reaction equation
[C:1]1([NH2:15])[N:2]=[C:3]([NH2:14])[N:4]=[C:5]2[C:10]=1[C:9]1[CH:11]=[CH:12][NH:13][C:8]=1[CH:7]=[CH:6]2.CN(C)C=O.[H-].[Na+].F[C:24]1[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][CH:25]=1>C(O)(=O)C>[C:28]([C:27]1[CH:30]=[CH:31][C:24]([N:13]2[C:8]3[CH:7]=[CH:6][C:5]4[C:10](=[C:1]([NH2:15])[N:2]=[C:3]([NH2:14])[N:4]=4)[C:9]=3[CH:11]=[CH:12]2)=[CH:25][CH:26]=1)#[N:29]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 145174-FluorobenzonitrileHCID 24758Sodium hydrideHCID 178508668HCID 178508668, compound

Product 1

HCID 22767691HCID 22767691, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 15.94 g. 7H-pyrrolo[3,2-f]quinazoline-1,3-diamine in 800 ml. dry dimethylformamide is stirred, under nitrogen, with 4.61 g. ca. 50% sodium hydride-mineral oil dispersion for 1.5 hours. Addition of 10.66 g. 4-fluorobenzonitrile is followed by heating of the reaction mixture at 95° for 6 hours. Glacial acetic acid (40 ml.) is added and the solvent is removed in vacuo. The residue is stirred thoroughly with excess aqueous potassium carbonate solution, collected, washed with water and dried. Two recrystallizations of the crude product from dimethylformamide, followed by washing with a small amount of dimethylformamide, with methanol and thorough drying, yield the title compound, m.p. 344° (dec.), NMR (dDMSO): δ 7.17 (doublet, J=9Hz, 5 or 6H), 7.42 (doublet, J=3Hz, 9H), 7.76-7.95 (four protons multiplet, 5 or 6H, 8H and two protons meta to the cyano group), 8.09 (two proton doublet, J= 8Hz, two protons ortho to the cyano group) p.p.m.

Workup

  1. additionAddition of 10.66 g
  2. temperatureby heating of the reaction mixture at 95° for 6 hours
  3. customthe solvent is removed in vacuo
  4. customcollected
  5. washwashed with water
  6. customdried
  7. customTwo recrystallizations of the crude product from dimethylformamide
  8. washby washing with a small amount of dimethylformamide, with methanol and thorough drying

Sources & evidence

ORD record
ord-f72eff676ce54b91bd450d7fa438f227
Source dataset
uspto-grants-1978_10
Patent number
US04118561

Reaction notes

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