Triethylamine → Methanesulfonic acid 2-[3-tert-butyl-5-(3-{4-[7-(4-methanesulfonyl-phenyl)-imidazo[1,2-a]pyridin-3-yl]-benzyl}-ureido)-pyrazol-1-yl]-ethyl ester

HRID 1446733Notes

Reaction equation

HRID 1446733 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:13][C:14]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[N:28]4[CH:29]=[CH:30][C:31]([C:33]5[CH:38]=[CH:37][C:36]([S:39]([CH3:42])(=[O:41])=[O:40])=[CH:35][CH:34]=5)=[CH:32][C:27]4=[N:26][CH:25]=3)=[CH:20][CH:19]=2)=[O:15])[N:8]([CH2:10][CH2:11][OH:12])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:50][S:51](Cl)(=[O:53])=[O:52]>C(Cl)Cl>[C:1]([C:5]1[CH:6]=[C:7]([NH:13][C:14]([NH:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]3[N:28]4[CH:29]=[CH:30][C:31]([C:33]5[CH:34]=[CH:35][C:36]([S:39]([CH3:42])(=[O:40])=[O:41])=[CH:37][CH:38]=5)=[CH:32][C:27]4=[N:26][CH:25]=3)=[CH:22][CH:23]=2)=[O:15])[N:8]([CH2:10][CH2:11][O:12][S:51]([CH3:50])(=[O:53])=[O:52])[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 578634381-[5-tert-Butyl-2-(2-hydroxy-ethyl)-2H-pyrazol-3-yl]-3-{4-[7-(4-methanesulfonyl-phenyl)-imidazo[1,2-a]pyridin-3-yl]-benzyl}-urea

Product 1

HCID 86634307Methanesulfonic acid 2-[3-tert-butyl-5-(3-{4-[7-(4-methanesulfonyl-phenyl)-imidazo[1,2-a]pyridin-3-yl]-benzyl}-ureido)-pyrazol-1-yl]-ethyl esterYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a round bottomed flask dissolve 1-[5-tert-butyl-2-(2-hydroxy-ethyl)-2H-pyrazol-3-yl]-3-{4-[7-(4-methanesulfonyl-phenyl)-imidazo[1,2-a]pyridin-3-yl]-benzyl}-urea (0.2 g, 0.34 mmol) and triethyl amine (0.48 mL, 10 equiv.) in DCM (20 mL) under N2. Add methanesulfonyl chloride (0.13 mL, 4.8 equiv.) dropwise and stir the reaction at room temperature for 15 minutes. Load the crude reaction directly onto silica gel and purify (EtOAc to 5% MeOH: DCM) to give a yellow solid (0.22 g, 97%). MS (ES), m/z 665 (M+1).

Workup

  1. customthe reaction at room temperature for 15 minutes
  2. customLoad the crude reaction directly onto silica gel
  3. custompurify (EtOAc to 5% MeOH: DCM)

Sources & evidence

ORD record
ord-b46eba72813e4e8fb381fbd57062fd43
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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