Oxalyl chloride → N-[2-(3-Dimethylamino-pyrrolidin-1-yl)-benzooxazol-5-yl]-3-(4-fluoro-phenyl)-acrylamide

HRID 1174920Notes

Reaction equation

HRID 1174920 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=O)=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[CH3:19][N:20]([CH3:36])[CH:21]1[CH2:25][CH2:24][N:23]([C:26]2[O:27][C:28]3[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][C:29]=3[N:30]=2)[CH2:22]1>>[CH3:19][N:20]([CH3:36])[CH:21]1[CH2:25][CH2:24][N:23]([C:26]2[O:27][C:28]3[CH:34]=[CH:33][C:32]([NH:35][C:8](=[O:10])[CH:7]=[CH:6][C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:12][CH:11]=4)=[CH:31][C:29]=3[N:30]=2)[CH2:22]1

Participants

4

Reactant 3

HCID 65578Oxalyl chlorideHCID 980703-(4-Fluorophenyl)-2-propenoic acidHCID 687717302-(3-Dimethylamino-pyrrolidin-1-yl)-benzooxazol-5-ylamine

Product 1

HCID 68770527N-[2-(3-Dimethylamino-pyrrolidin-1-yl)-benzooxazol-5-yl]-3-(4-fluoro-phenyl)-acrylamideYield 69.3%

Procedure

Prepare according to Method C (Example 9), using 4-fluorocinnamic acid (107 mg, 0.643 mmol), oxalyl chloride (300 μL, 3.43 mmol), and 2-(3-dimethylamino-pyrrolidin-1-yl)-benzooxazol-5-ylamine (97 mg, 0.399 mmol) to afford the title compound (109 mg, 69%). mass spectrum (m/e): 395.3 [M+H], 393.3 [M−H]. 1H NMR (400 MHz, CDCl3): δ 7.68 (m, 1H), 7.53-7.35 (m, 4H), 7.17 (m, 1H), 7.07-6.95 (m, 2H), 6.49 (d, 1H, J=15.4 Hz), 3.94-3.77 (m, 2H), 3.59 (m, 1H), 3.44 (m, 1H), 2.89 (m, 1H), 2.31 (s, 6H), 2.24 (m, 1H), 1.96 (m, 1H).

Workup

  1. customPrepare

Sources & evidence

ORD record
ord-96e00da4a08b444bb254ec897ddbbe50
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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