Formaldehyde → HCID 22140729, compound

HRID 1826264Notes

Reaction equation

HRID 1826264 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-methoxyinilino)-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-37e2eea6cead4b60998a1a78de0d1e7c
Source dataset
uspto-grants-2006_05
Patent number
US07049438B2

Reaction notes

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