Diethyl Ether → HCID 10202900, compound

HRID 2084438Notes

Reaction equation

HRID 2084438 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][C:17]1[CH:21]=[C:20]([CH3:22])[NH:19][C:18]=1[CH:23]=[C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[NH:26][C:25]1=[O:33].CN(C1C=CC=CN=1)C.CCOCC>CN(C=O)C>[CH3:16][C:17]1[CH:21]=[C:20]([CH3:22])[NH:19][C:18]=1/[CH:23]=[C:24]1\[C:25](=[O:33])[N:26]([C:13](=[O:15])[CH2:12][NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:27]2[C:32]\1=[CH:31][CH:30]=[CH:29][CH:28]=2

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14349BenzyloxycarbonylglycineHCID 218852-DimethylaminopyridineHCID 123015Semaxinib

Product 1

HCID 10202900HCID 10202900, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of N-(benzyloxycarbonyl)glycine (4.9 g, 23 mmol), 3-(3,5-dimethyl-1H-pyrrol-2-ylmethylidene)-1,3-dihydro-indol-2-one (2.38 g, 10 mmol), dimethylaminopyridine (1.28 g, 10 mmol) in DMF (20 mL) was heated at 55° C. for 2 h. The solution was cooled, ether (10 mL) was added and the precipitate of the title compound was filtered off and dried to give 2.35 g, mp 193-196+ C. HPLC Rt 7.04 min. 1H NMR (CDCl3) δ2.34 (s, 3H), 2.42 (s, 3H), 4.87 (d, 2H), 5.18 (s, 2H), 5.74 (t, 1H), 6.06 (d, 1H), 7.2 (m, 3H), 7.3-7.65 (m, 7H), 7.49 (m, 1H), and 8.23 (m, 1H), for C25H23N3O4: C, 69.92; H, 5.40; N, 9.78. Found: C, 69.91; H, 5.50; N, 9.86.

Workup

  1. temperatureThe solution was cooled
  2. filtrationthe precipitate of the title compound was filtered off
  3. customdried
  4. customto give 2.35 g, mp 193-196+ C

Sources & evidence

ORD record
ord-e26044f7d11143b7a8868354326498e9
Source dataset
uspto-grants-2004_04
Patent number
US06716870B2

Reaction notes

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