Methylamine → N-Cyclopropyl-4-methyl-3-[3-(2-{2-[3-(methylamino)propoxy]phenyl}pyrrolidin-1-yl)-2-oxopyrazin-1(2H)-yl]benzamide

HRID 337160Notes

Reaction equation

HRID 337160 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:12]1[CH2:16][CH2:15][CH2:14][N:13]1[C:17]1[C:18](=[O:36])[N:19]([C:23]2[CH:24]=[C:25]([CH:32]=[CH:33][C:34]=2[CH3:35])[C:26]([NH:28][CH:29]2[CH2:31][CH2:30]2)=[O:27])[CH:20]=[CH:21][N:22]=1.[CH3:37][NH2:38]>O1CCOCC1>[CH:29]1([NH:28][C:26](=[O:27])[C:25]2[CH:32]=[CH:33][C:34]([CH3:35])=[C:23]([N:19]3[CH:20]=[CH:21][N:22]=[C:17]([N:13]4[CH2:14][CH2:15][CH2:16][CH:12]4[C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=4[O:5][CH2:4][CH2:3][CH2:2][NH:38][CH3:37])[C:18]3=[O:36])[CH:24]=2)[CH2:31][CH2:30]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 666892263-[3-{2-[2-(3-Chloropropoxy)phenyl]pyrrolidin-1-yl}-2-oxopyrazin-1(2H)-yl]-N-cyclopropyl-4-methylbenzamide

Product 1

HCID 66685834N-Cyclopropyl-4-methyl-3-[3-(2-{2-[3-(methylamino)propoxy]phenyl}pyrrolidin-1-yl)-2-oxopyrazin-1(2H)-yl]benzamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-[3-{2-[2-(3-Chloropropoxy)phenyl]pyrrolidin-1-yl}-2-oxopyrazin-1(2H)-yl]-N-cyclopropyl-4-methylbenzamide (Example 324b, 0.23 g) and methylamine (1 mL) were heated in a CEM microwave in dioxane at 110° C. for 15 min. The resulting solution was concentrated in vacuo and purification by preparative HPLC (X-Bridge column using a 95-5% gradient of aqueous 0.2% ammonia in acetonitrile) gave the title compound as a solid (0.028 g).

Workup

  1. concentrationThe resulting solution was concentrated in vacuo and purification by preparative HPLC (X-Bridge column

Sources & evidence

ORD record
ord-1221dda3749a48eeb95433a03e7f1806
Source dataset
uspto-grants-2014_11
Patent number
US08889692B2

Reaction notes

Loading…