Triethylamine → N-(1-{3-[(pyridin-4-ylmethyl)oxy]pyrazin-2-yl}pyrrolidin-3-yl)-N'-[3-(trifluoro-methyl)phenyl]urea

HRID 907564Notes

Reaction equation

HRID 907564 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[C:10]([N:15]3[CH2:19][CH2:18][CH:17]([NH2:20])[CH2:16]3)=[N:11][CH:12]=[CH:13][N:14]=2)=[CH:3][CH:2]=1.C(N(CC)CC)C.[N:28]([C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[CH:32]=1)=[C:29]=[O:30]>ClCCl>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[C:10]([N:15]3[CH2:19][CH2:18][CH:17]([NH:20][C:29]([NH:28][C:31]4[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:38])([F:39])[F:40])[CH:32]=4)=[O:30])[CH2:16]3)=[N:11][CH:12]=[CH:13][N:14]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 590138991-[3-(Pyridin-4-ylmethoxy)-pyrazin-2-yl]-pyrrolidin-3-ylamine

Product 1

HCID 59013784N-(1-{3-[(pyridin-4-ylmethyl)oxy]pyrazin-2-yl}pyrrolidin-3-yl)-N'-[3-(trifluoro-methyl)phenyl]ureaYield 16%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[3-(pyridin-4-ylmethoxy)-pyrazin-2-yl]-pyrrolidin-3-ylamine (50 mg, 0.18 mmole), triethylamine (excess eq.) in dichloromethane was added 1-isocyanato-3-trifluoromethyl-benzene (37 mg, 0.198 mmole). The mixture was stirred at room temperature for 1 hour. The mixture was then concentrated in vacuo, and purified by preparative HPLC to give N-(1-{3-[(pyridin-4-ylmethyl)oxy]pyrazin-2-yl}pyrrolidin-3-yl)-N′-[3-(trifluoro-methyl)phenyl]urea (13.2 mg, 12.5% yield). 1H NMR (DMSO-d6) 8.80 (m, 3H), 7.97 (s, 1H), 7.90 (d, 2H), 7.68 (d, 1H), 7.4 (m, 2H), 7.3 (d, 1H), 7.2 (m, 1H), 6.8 (d, 1H), 5.3 (s, 2H), 4.25 (m, H), 3.9 (m, 1H), 3.75 (m, 2H), 3.6 (m, 1H), 2.40 (m, 1H), 1.85 (m, 1H) ppm.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-63ce5eace736471baf289a09f4949869
Source dataset
uspto-grants-2011_09
Patent number
US08013156B2

Reaction notes

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