Formaldehyde → HCID 178424865, compound

HRID 2214471Notes

Reaction equation

HRID 2214471 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) δ 2.34 (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 recrystsllized 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-0fb4fef3c1254a8da7456a0e84d0a336
Source dataset
uspto-grants-2006_09
Patent number
US07109185B2

Reaction notes

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