Formaldehyde → HCID 66918964, compound

HRID 2354227Notes

Reaction equation

HRID 2354227 reaction equation
[CH:1]1([NH:4][C:5](=[O:30])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([C:24]5[CH2:25][CH2:26][NH:27][CH2:28][CH:29]=5)[CH:20]=4)[N:15]=[CH:14]3)[CH:7]=2)[CH2:3][CH2:2]1.[CH2:31]=O>C(O)=O>[CH:1]1([NH:4][C:5](=[O:30])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([C:24]5[CH2:25][CH2:26][N:27]([CH3:31])[CH2:28][CH:29]=5)[CH:20]=4)[N:15]=[CH:14]3)[CH:7]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 11258090HCID 11258090, compound

Product 1

HCID 66918964HCID 66918964, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

N-Cyclopropyl-4-methyl-3-[4-oxo-6-(1,2,3,6-tetrahydropyridin-4-yl)quinazolin-3(4H)-yl]benzamide (0.293 g) and 38% aqueous formaldehyde (0.577 ml) were stirred in formic acid (6 ml) at 90° C. for 3.5 hours and then concentrated. The residue was partitioned between ethyl acetate and saturated aqueous NaHCO3 solution. The organic layer was washed with brine, dried (magnesium sulfate) and concentrated. Purification by column chromatography on a silica column eluting with 10% methanol/ethyl acetate followed by 10% methanol/ethyl acetate+1% aqueous ammonia solution to give N-cyclopropyl-4-methyl-3-[6-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-4-oxoquinazolin-3(4H)-yl]benzamide (AZ12285777) (0.257 g) as a white foam solid; NMR Spectrum: (DMSOd6) 0.55 (m, 2H), 0.70 (m, 2H), 2.15 (s, 3H), 2.30 (s, 3H), 2.59 (m, 4H), 2.85 (m, 1H), 3.08 (s, 2H), 6.40 (s, 1M), 7.52 (d, 1H), 7.74 (d, 1H), 7.85 (s, 1H), 7.91 (d, 1H), 8.06 (d, 1H), 8.14 (s, 1H), 8.29 (s, 1H), 8.43 (d, 1H); Mass Spectrum: M+H+ 415.

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between ethyl acetate and saturated aqueous NaHCO3 solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated
  6. customPurification by column chromatography on a silica column
  7. washeluting with 10% methanol/ethyl acetate

Sources & evidence

ORD record
ord-39993cefd8f0473bafb37bdb85d581de
Source dataset
uspto-grants-2010_07
Patent number
US07750154B2

Reaction notes

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