4-Methoxy cinnamic acid → N-[2-(3-Dimethylamino-pyrrolidin-1-yl)-benzooxazol-5-yl]-3-(4-methoxy-phenyl)-acrylamide

HRID 1174919Notes

Reaction equation

HRID 1174919 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([OH:11])=O)=[CH:5][CH:4]=1.C(Cl)(=O)C(Cl)=O.[CH3:20][N:21]([CH3:37])[CH:22]1[CH2:26][CH2:25][N:24]([C:27]2[O:28][C:29]3[CH:35]=[CH:34][C:33]([NH2:36])=[CH:32][C:30]=3[N:31]=2)[CH2:23]1>>[CH3:20][N:21]([CH3:37])[CH:22]1[CH2:26][CH2:25][N:24]([C:27]2[O:28][C:29]3[CH:35]=[CH:34][C:33]([NH:36][C:9](=[O:11])[CH:8]=[CH:7][C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:13][CH:12]=4)=[CH:32][C:30]=3[N:31]=2)[CH2:23]1

Participants

4

Reactant 3

HCID 132454-Methoxy cinnamic acidHCID 65578Oxalyl chlorideHCID 687717302-(3-Dimethylamino-pyrrolidin-1-yl)-benzooxazol-5-ylamine

Product 1

HCID 68772527N-[2-(3-Dimethylamino-pyrrolidin-1-yl)-benzooxazol-5-yl]-3-(4-methoxy-phenyl)-acrylamideYield 72.2%

Procedure

Prepare according to Method C (Example 9), using 4-methoxycinnamic acid (110 mg, 0.617 mmol), oxalyl chloride (300 μL, 3.43 mmol), and 2-(3-dimethylamino-pyrrolidin-1-yl)-benzooxazol-5-ylamine (99 mg, 0.402 mmol) to afford the title compound (118 mg, 72%). mass spectrum (m/e): 407.4 [M+H], 405.3 [M−H].

Workup

  1. customPrepare

Sources & evidence

ORD record
ord-506caba3b5ea427a81e82f75ddd08f1a
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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