Formaldehyde → HCID 9924560, compound

HRID 2084435Notes

Reaction equation

HRID 2084435 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH2:8]=O.[CH3:10][C:11]1[CH:15]=[C:14]([CH3:16])[NH:13][C:12]=1[CH:17]=[C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:20][C:19]1=[O:27]>CO>[CH3:10][C:11]1[CH:15]=[C:14]([CH3:16])[NH:13][C:12]=1/[CH:17]=[C:18]1\[C:19](=[O:27])[N:20]([CH2:1][N:2]2[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]2)[C:21]2[C:26]\1=[CH:25][CH:24]=[CH:23][CH:22]=2

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 531671-MethylpiperazineHCID 123015Semaxinib

Product 1

HCID 9924560HCID 9924560, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

N-Methylpiperazine (10 g, 100 mmol) was added to a stirred solution of aqueous formaldehyde (10 g of 38% solution, 100 mmol) and 3-(3,5-dimethyl-1H-pyrrol-2-ylmethylidene)-1,3-dihydro-indol-2-one, (2.38 g, 10 mmol) in methanol (100 mL). The solution heated at 60° C. for 1 h, concentrated to a low volume and the precipitate was filtered off, washed with methanol, and dried to give 2.38 g of the title compound, mp 160-164° C. HPLC Rt 4.72 min. 1H NMR (CDCl3) δ2.26 (s, 3H), 2.33 (s, 3H), 2.38 (s, 3H), 2.43 (br s, 4H), 2.70 (br s, 4H), 4.59 (s, 2H), 5.96 (d, 1H), 7.02-7.08 (m, 2H), 7.15 (dd, 1H), 7.38 (s, 1H), 7.48 (dd, 1H) and 13.0 (br s, 1H). Anal. Calcd for C21H26N4O: C, 71.97; H, 7.48; N, 15.99. Found: C, 71.75; H, 7.46; N, 15.87.

Workup

  1. concentrationconcentrated to a low volume
  2. filtrationthe precipitate was filtered off
  3. washwashed with methanol
  4. customdried

Sources & evidence

ORD record
ord-62e6bdbe002c45af88eeb21ed40d1b35
Source dataset
uspto-grants-2004_04
Patent number
US06716870B2

Reaction notes

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