4-(2-Propyn-1-yl)morpholine → 1-(3,5-Dichloro-pyridin-4-ylmethyl)-6-methoxy-5-(3-morpholin-4-yl-prop-1-ynyl)-phthalazine

HRID 2297500Notes

Reaction equation

HRID 2297500 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:29])[C:7]=1[CH2:8][C:9]1[C:18]2[C:13](=[C:14](OS(C(F)(F)F)(=O)=O)[C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[CH:12]=[N:11][N:10]=1.[CH2:30]([N:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1)[C:31]#[CH:32]>C(NCC)C>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:29])[C:7]=1[CH2:8][C:9]1[C:18]2[C:13](=[C:14]([C:32]#[C:31][CH2:30][N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)[C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[CH:12]=[N:11][N:10]=1

Participants

4

Reactant 2

HCID 4129414-(2-Propyn-1-yl)morpholineHCID 53981658Trifluoro-methanesulfonic acid 1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-phthalazin-5-yl ester

Product 1

HCID 183816721-(3,5-Dichloro-pyridin-4-ylmethyl)-6-methoxy-5-(3-morpholin-4-yl-prop-1-ynyl)-phthalazineYield 38.6%

Reagents, catalysts & solvents 1

HCID 8021DiethylamineSolvent

Procedure

Operating analogously to what described in example 74 starting from trifluoro-methanesulfonic acid 1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-phthalazin-5-yl ester (2 g, 4.27 mmoles), prepared as described in example 73, 4-prop-2-ynyl-morpholine (640 mg, 5.12 mmoles), prepared as described in example 137, diethylamine (40 ml), bis(triphenylphosphine)PdCl2 (60 mg, 0.0854 mmole) and Cul (16 mg, 0.0854 mmole), 728 mg of the title compound were obtained (yield: 38.6%).

Workup

  1. customprepared
  2. customprepared

Sources & evidence

ORD record
ord-bfa5111f7ab84e8aa11f9fc753460f4f
Source dataset
uspto-grants-2002_12
Patent number
US06492360B1

Reaction notes

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