4-Hydroxypyrrolidine → 11-Ethyl-2-(3-hydroxypyrrolidin-1-yl)-4-methyl-5,11-dihydro-6H-dipyrido[2,3-e:3',2'-b][1,4]diazepin-6-one

HRID 2380257

Reaction equation

HRID 2380257 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH3:20])[C:5]2[NH:6][C:7](=[O:19])[C:8]3[CH:18]=[CH:17][CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1.[OH:21][CH:22]1[CH2:26][CH2:25][NH:24][CH2:23]1>O>[CH2:13]([N:10]1[C:9]2[N:15]=[CH:16][CH:17]=[CH:18][C:8]=2[C:7](=[O:19])[NH:6][C:5]2[C:4]([CH3:20])=[CH:3][C:2]([N:24]3[CH2:25][CH2:26][CH:22]([OH:21])[CH2:23]3)=[N:12][C:11]1=2)[CH3:14]

Participants

4

Reactant 2

HCID 982104-HydroxypyrrolidineHCID 463144Dipyridodiazepinone deriv. 15

Product 1

HCID 46354911-Ethyl-2-(3-hydroxypyrrolidin-1-yl)-4-methyl-5,11-dihydro-6H-dipyrido[2,3-e:3',2'-b][1,4]diazepin-6-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
170 °C

Procedure

A suspension of the 2-chloro-5,11-dihydro-11-ethyl-4-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.14 g) in 3-hydroxypyrrolidine (0.29 g) in an open test tube was heated at 170° C. for 30 minutes. After cooling to room temperature the mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed, dried, and evaporated. Chromatography over silica gel with ethyl acetate gave the title compound, which crystallized from ethyl acetate. Yield, 0.12 g, m.p. 131°-134° C.

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-a8e1e43b5eed47839f6ad2584eba7420
Source dataset
uspto-grants-1994_11
Patent number
US05366972

Linked notes

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