Formic Acid → 7-chloro-3-{3-methoxy-4-[2-(1-pyrrolidinyl)ethoxy]phenyl}-4(3H)-quinazolinone

HRID 1181363Notes

Reaction equation

HRID 1181363 reaction equation
[NH2:1][C:2]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[C:9]([O:21][CH3:22])[CH:8]=1)=[O:5].[CH:28](O)=O>>[Cl:27][C:25]1[CH:26]=[C:2]2[C:3]([C:4](=[O:5])[N:6]([C:7]3[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][N:16]4[CH2:17][CH2:18][CH2:19][CH2:20]4)=[C:9]([O:21][CH3:22])[CH:8]=3)[CH:28]=[N:1]2)=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 589808752-amino-4-chloro-N-{3-methoxy-4-[2-(1-pyrrolidinyl)ethoxy]phenyl}benzamide

Product 1

HCID 589808727-chloro-3-{3-methoxy-4-[2-(1-pyrrolidinyl)ethoxy]phenyl}-4(3H)-quinazolinoneYield 91%

Procedure

2-Amino-4-chloro-N-{3-methoxy-4-[2-(1-pyrrolidinyl)ethoxy]phenyl}benzamide (11.6 mmol, 4.5 g) was dissolved in 90 mL 88% formic acid and was heated to reflux for 3 h. The solvents were removed by rotary evaporation and the residue was purified by silica gel column chromatography affording the lo product (4.2 g, 91%). 1H NMR (DMSO-D6): δ 1.82 (4H, m), 2.65 (4H, m), 2.88 (2H, t, J=6.2 Hz), 3.88 (3H, s), 4.20 (2H, t, J=6.4 Hz), 6.89-6.91 (2H, overlapping), 7.01 (1H, d, J=10.1 Hz), 7.49 (1H, d, J=8.6 Hz), 7.76 (1H, s), 8.12 (1H, s), 8.29 (1H, d, 8.7 Hz). LCMS m/z=400 (m+H+).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. customThe solvents were removed by rotary evaporation
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-85f125b9502a4f3a818a44efcb6c6fe6
Source dataset
uspto-grants-2007_10
Patent number
US07285557B2

Reaction notes

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