Dimethylamine → HCID 58235079, compound

HRID 1187181Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]([C:11]2[CH:12]=[C:13]([C:28](O)=[O:29])[CH:14]=[C:15]3[C:20]=2[O:19][C:18]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[CH:17][C:16]3=[O:27])[CH3:10])=[CH:4][CH:3]=1.[CH3:31][NH:32][CH3:33]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH:9]([C:11]2[CH:12]=[C:13]([C:28]([N:32]([CH3:33])[CH3:31])=[O:29])[CH:14]=[C:15]3[C:20]=2[O:19][C:18]([N:21]2[CH2:22][CH2:23][O:24][CH2:25][CH2:26]2)=[CH:17][C:16]3=[O:27])[CH3:10])=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 674Dimethylamine

HCID 58235003HCID 58235003, compound

Product 1

HCID 58235079HCID 58235079, compoundYield 60.7%

Procedure

8-(1-(4-fluorophenylamino)ethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid (82 mg, 0.20 mmol) was reacted with dimethylamine (0.119 mL, 0.24 mmol) using a procedure similar to the one described in Example 2.00 to afford 8-(1-(4-fluorophenylamino)ethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (53 mg, 60.7%) as a white solid. Mass Spectrum: M+H+ 440. NMR Spectrum: (DMSOd6) 1.50 (d, 3H), 2.66 (s, 3H), 2.92 (s, 3H), 3.50-3.65 (m, 4H), 3.70-3.81 (m, 4H), 4.92-5.02 (m, 1H), 5.60 (s, 1H), 6.27 (d, 1H), 6.46 (dd, 2H), 6.84 (dd, 2H), 7.56 (d, 1H), 7.77 (d, 1H).

Sources & evidence

ORD record: ord-6dcb1990feaa453494721617bc2faed4
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673906B2

Reaction notes

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