Formaldehyde → HCID 178424865, compound

HRID 1018643Notes

Reaction equation

HRID 1018643 reaction equation
[CH2:1]=[O:2].[CH3:3][C:4]1[CH:8]=[C:7]([CH3:9])[NH:6][C:5]=1[CH:10]=[C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][C:12]1=[O:20].C(N(CC)CC)C>CN(C)C=O.O>[CH3:3][C:4]1[CH:8]=[C:7]([CH3:9])[NH:6][C:5]=1/[CH:10]=[C:11]1\[C:12](=[O:20])[N:13]([CH2:1][OH:2])[C:14]2[C:19]\1=[CH:18][CH:17]=[CH:16][CH:15]=2

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 8471TriethylamineHCID 123015Semaxinib

Product 1

HCID 178424865HCID 178424865, compoundYield 98.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Aqueous formaldehyde (15.0 g of 38% solution, 190 mmol) was added to a stirred solution of 3-(3,5-dimethyl-1H-pyrrol-2-ylmethylidene)-1,3-dihydro-indol-2-one (23.8 g, 100 mmol) and triethylamine (15.0 g, 150 mmol) in dimethylformamide (200 mL). After 1 h, the solution was diluted with water and the precipitate was filtered off, washed with water, and dried to give 26.4 g of the title compound, mp 196-200° C. HPLC Rt 5.71 min. 1H NMR (CDCl3) δ2.34 (s, 6H), 3.14 (t, 1H), 5.44 (d, 2H), 5.98 (d, 1H), 7.08 (m, 2H), 7.18 (m, 1H), 7.36 (s, 1H), 7.48 (dd, 1H) and 13.0 (br s, 1H). Anal. Calcd for C16H16N2O2: C, 71.62; H, 6.01; N, 10.44. Found: C, 71.33; H, 6.09; N, 10.43. A sample was recrystallized from ethyl acetate; mp 200-202° C.

Workup

  1. filtrationthe precipitate was filtered off
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-3e8913977eca44efa2772ae1c69a4990
Source dataset
uspto-grants-2002_11
Patent number
US06482848B2

Reaction notes

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