Ethanolamine → 9-[2-(2-Hydroxyethylamino)ethyl]-2,4-di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indole

HRID 482326Notes

Reaction equation

HRID 482326 reaction equation
CS(O[CH2:6][CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]2[C:17]([N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)=[N:18][C:19]([N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[N:20][C:9]1=2)(=O)=O.[CH2:31]([CH2:33][NH2:34])[OH:32]>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[OH:32][CH2:31][CH2:33][NH:34][CH2:6][CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]2[C:17]([N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)=[N:18][C:19]([N:21]3[CH2:22][CH2:23][CH2:24][CH2:25]3)=[N:20][C:9]1=2

Participants

5

Reactant 2

HCID 700EthanolamineHCID 537324089-(2-Methanesulfonyloxyethyl)-2,4-di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indole

Product 1

HCID 538747549-[2-(2-Hydroxyethylamino)ethyl]-2,4-di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indole

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 9-(2-methanesulfonyloxyethyl)-2,4-di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indole (IX, EXAMPLE 4, 1.3 g) and 15 ml of ethanolamine is heated to reflux for 4 hr, then cooled, and diluted with methylene chloride (100 mL) and aqueous saturated sodium bicarbonate. The phases are separated, and the aqueous phase is extracted again with methylene chloride/chloroform (1/1). The combined extracts are dried over sodium sulfate and concentrate under reduced pressure at 50°-60° to give a solid. The solid is recrystallized from ethyl acetate/hexane at 20°-250 to give the title compound, NMR (CDCl3) 1.5-1.7, 1.9-2.0, 2.84, 3.12, 3.56, 3.63, 3.92, 4.20, 7.10, 7.13-7.30 and 7.80 δ; MS (EI, m/z) 394 (M+), 363, 320 and 307.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 4 hr
  3. temperaturecooled
  4. customThe phases are separated
  5. extractionthe aqueous phase is extracted again with methylene chloride/chloroform (1/1)
  6. dry with materialThe combined extracts are dried over sodium sulfate
  7. concentrationconcentrate under reduced pressure at 50°-60°
  8. customto give a solid
  9. customThe solid is recrystallized from ethyl acetate/hexane at 20°-250

Sources & evidence

ORD record
ord-cd1cf6f8cba34f14b250adedb6ba314a
Source dataset
uspto-grants-1998_08
Patent number
US05795986

Reaction notes

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