Acetic Acid → HCID 118274291, compound

HRID 522214Notes

Reaction equation

HRID 522214 reaction equation
C=O.C(O)(=O)C.[F:7][C:8]1[CH:9]=[CH:10][C:11]2[N:20]([CH3:21])[CH2:19][C:18]3[C:14]4[C:15](=[N:24][CH:25]=[CH:26][C:13]=4[C:12]=2[CH:27]=1)[N:16](CO)[CH:17]=3>O>[F:7][C:8]1[CH:9]=[CH:10][C:11]2[N:20]([CH3:21])[CH2:19][C:18]3[C:14]4[C:15](=[N:24][CH:25]=[CH:26][C:13]=4[C:12]=2[CH:27]=1)[NH:16][CH:17]=3

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 712FormaldehydeHCID 118274175HCID 118274175, compound

Product 1

HCID 118274291HCID 118274291, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of paraformaldehyde (12.76 g, 425 mmol), Example 41A (20.5 g, 85 mmol) and acetic acid (243 mL) was stirred at room temperature overnight. The mixture was poured into water and the solid was collected by filtration to provide a mixture of the title compound and (7-fluoro-4-methyl-3,4-dihydro-1H-1,4,11-triazadibenzo[cd,f]azulen-1-yl)methanol. To a solution of this mixture in acetonitrile (506 mL) at room temperature was added 5N aqueous sodium hydroxide (122 mL, 608 mmol) and the mixture was heated at 60° C. for 1 hour. The mixture was cooled to room temperature and poured into water. The solid was collected by filtration to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ 11.42 (s, 1H), 8.26 (d, J=5.2 Hz, 1H), 7.75 (dd, J=10.6, 3.0 Hz, 1H), 7.35 (d, J=5.3 Hz, 1H), 7.32-7.13 (m, 3H), 4.12 (s, 2H), 2.87 (s, 3H). MS (ESI+) m/z 254.3 (M+H)+.

Workup

  1. filtrationthe solid was collected by filtration
  2. customto provide

Sources & evidence

ORD record
ord-274162779151425a8a7d2aa921a41416
Source dataset
uspto-grants-2016_05
Patent number
US09328112B2

Reaction notes

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