Formaldehyde → HCID 9927128, compound

HRID 49998Notes

Reaction equation

HRID 49998 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:6]=O.[CH3:8][C:9]1[CH:13]=[C:12]([CH3:14])[NH:11][C:10]=1[CH:15]=[C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[NH:18][C:17]1=[O:25]>CO>[CH3:8][C:9]1[CH:13]=[C:12]([CH3:14])[NH:11][C:10]=1/[CH:15]=[C:16]1\[C:17](=[O:25])[N:18]([CH2:6][N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[C:19]2[C:24]\1=[CH:23][CH:22]=[CH:21][CH:20]=2

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 31268PyrrolidineHCID 123015Semaxinib

Product 1

HCID 9927128HCID 9927128, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Pyrrolidine (450 mg, 6.3 mmol) was added to a stirred solution of aqueous formaldehyde (500 mg of 38% solution, 6.0 mmol) and 3-(3,5-dimethyl-1H-pyrrol-2-ylmethylidene)-1,3-dihydro-indol-2-one (900 mg, 3.8 mmol) in methanol (50 mL). After 15 min., the solution was cooled to 0° C. and the precipitate was filtered off, washed with water, and dried to give 1.08 g of the title compound, mp 129-132° C. HPLC Rt 4.87 min. 1H NMR [(CD3)2SO] δ1.65 (m, 4H), 2.32 9s, 3H), 2.34 (s, 3H), 2.62 (m, 4H), 4.72 (s, 2H) 6.07 (d, 1H), 7.00 (m, 1H), 7.15 (m, 2H), 7.61 (s, 1H), 7.76 (d, 2H) and 13.1 (br s, 1H). Anal. Calcd for C20H23N3O: C, 74.74; H, 7.21; N, 13.07. Found: C, 74.61; H, 7.25; N, 13.03.

Workup

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

Sources & evidence

ORD record
ord-33696b0f91b24b929131e73b8dab46e6
Source dataset
uspto-grants-2004_03
Patent number
US06710067B2

Reaction notes

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