Triethylamine → 9-(2-Methanesulfonyloxyethyl)-2,4-di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indole

HRID 482319Notes

Reaction equation

HRID 482319 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH2:8][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:18]([N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)=[N:19][C:20]([N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[N:21][C:10]1=2.C(N(CC)CC)C>C(Cl)Cl.O>[CH3:1][S:2]([O:6][CH2:7][CH2:8][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:18]([N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)=[N:19][C:20]([N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[N:21][C:10]1=2)(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 155216162-[2,4-Di(pyrrolidin-1-yl)-9H-pyrimido[4,5-b]indol-9-yl]ethan-1-ol

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of methanesulfonyl chloride (0.38 mL) in methylene chloride (20 mL) is added dropwise to a mixture of 9-(2-hydroxyethyl)-2,4-di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indole (VIII, EXAMPLE3, 1.05 g) and triethylamine (0.5 mL) in methylene chloride (25 mL). After a few minutes, the reaction mixture is diluted with water and extracted with methylene chloride. The organic layer is dried (sodium sulfate) and concentrated, to give the title compound.

Workup

  1. waitAfter a few minutes
  2. extractionextracted with methylene chloride
  3. dry with materialThe organic layer is dried (sodium sulfate)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1c1ac541387f4527b46d1695d7932ec6
Source dataset
uspto-grants-1998_08
Patent number
US05795986

Reaction notes

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