Formaldehyde → HCID 22140729, compound

HRID 1373277Notes

Reaction equation

HRID 1373277 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:17]=2[C:18]([NH:26][C:27]2[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[CH:29][C:28]=2[Cl:35])=[N:19][CH:20]=[N:21]3)[CH2:10][CH2:9]1)=O)(C)(C)C.C=O>C(O)=O>[Cl:35][C:28]1[CH:29]=[CH:30][C:31]([O:33][CH3:34])=[CH:32][C:27]=1[NH:26][C:18]1[C:17]2[C:22](=[CH:23][CH:24]=[CH:25][C:16]=2[O:15][CH2:14][CH:11]2[CH2:12][CH2:13][N:8]([CH3:6])[CH2:9][CH2:10]2)[N:21]=[CH:20][N:19]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 22140804HCID 22140804, compound

Product 1

HCID 22140729HCID 22140729, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-[N-(tert-butoxycarbonyl)piperidin-4-ylmethoxy]-4-(2-chloro-5-methoxyanilino)quinazoline (0.2 g), a concentrated aqueous formaldehyde solution (37%, 0.4 ml) and formic acid (4 ml) was stirred and heated to 100° C. for 2.5 hours. The mixture was cooled to ambient temperature and evaporated. The residue was triturated under diethyl ether and the resultant solid was isolated and dried under vacuum. There was thus obtained 4-(2-chloro-5-methoxyanilino)-5-(N-methylpiperidin-4-ylmethoxy)quinazoline, as a formic acid salt (0.09 g); NMR Spectrum: (CDCl3) 1.8–2.0 (m, 2H), 2.05–2.15 (m, 2H), 2.35 (m, 1H), 2.6 (t, 2H), 3.55 (d, 2H), 3.93 (s, 3H), 4.21 (d, 2H), 6.68 (m, 1H), 6.95 (d, 1H), 7.31 (d, 1H), 7.54 (d, 1H), 7.7 (m, 1H), 8.35 (br s, 1H), 8.39 (d, 1H), 8.7 (s, 1H); Mass Spectrum: M+H+ 413.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. customevaporated
  3. customThe residue was triturated under diethyl ether
  4. customthe resultant solid was isolated
  5. customdried under vacuum

Sources & evidence

ORD record
ord-7de4c3163b514c86927536e120985e45
Source dataset
uspto-grants-2007_01
Patent number
US07160891B2

Reaction notes

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