Methyl Acrylate → HCID 59733131, compound

HRID 1983307Notes

Reaction equation

[NH2:1][CH2:2][C:3]1[N:4]=[C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=2[C:19]([CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:20])=[O:10])[S:6][CH:7]=1.[C:26]([O:30][CH3:31])(=[O:29])[CH:27]=[CH2:28].C([O-])([O-])=[O:33].[Cs+].[Cs+].[CH2:38]1[CH2:42][O:41][CH2:40][CH2:39]1>>[CH3:31][O:30][C:26](=[O:29])[CH2:27][CH2:28][N:1]([CH2:2][C:3]1[N:4]=[C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=2[C:19]([CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:20])=[O:10])[S:6][CH:7]=1)[CH2:38][CH2:39][C:40]([O:41][CH3:42])=[O:33]

Participants

Reactant 4

HCID 7294Methyl Acrylate

HCID 8028Tetrahydrofuran

HCID 10796Cesium carbonate

HCID 597328161-(4-Aminomethyl-thiazol-2-yl)-3-(2-cyclopentanecarbonyl-4-methylphenyl)-urea

Product 1

HCID 59733131HCID 59733131, compoundYield 86%

Procedure

3-[{2-[3-(2-Cyclopentanecarbonyl-4-methyl-phenyl)-ureido]-thiazol-4-ylmethyl}-(2-methoxycarbonyl-ethyl)-amino]-propionic acid methyl ester (114 mg, 86%) was prepared by heating 1-(4-aminomethyl-thiazol-2-yl)-3-(2-cyclopentanecarbonyl-4-methyl-phenyl)-urea (90 mg, 0.25 mmol) with methyl acrylate (0.1 mL, 1.1 mmol) and Cs2CO3 (325 mg, 1.0 mmol) in THF (5 mL) at 60° C. for 2 h followed by column purification [silica, DCM:ethyl acetate (80:20 to 20:80)].

Workup

customfollowed by column purification [silica, DCM:ethyl acetate (80:20 to 20:80)]

Sources & evidence

ORD record: ord-104d770fae7d4cfa89ab8b0c902641a3
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07541373B2

Reaction notes

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