1,2-Ethanediamine, N1,N1,N2-trimethyl- → HCID 52913928, compound

HRID 1947294Notes

Reaction equation

HRID 1947294 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][N:32]([CH3:37])[CH2:33][CH2:34][NH:35][CH3:36]>>[CH3:31][N:32]([CH3:37])[CH2:33][CH2:34][N:35]([CH3:36])[C:28]([C:13]1[CH:14]=[C:15]2[C:20](=[C:11]([CH:9]([NH:8][C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH3:10])[CH:12]=1)[O:19][C:18]([N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1)=[CH:17][C:16]2=[O:27])=[O:29]

Participants

3

Reactant 2

HCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 58235003HCID 58235003, compound

Product 1

HCID 52913928HCID 52913928, compoundYield 15.9%

Procedure

8-(1-(4-fluorophenylamino)ethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid (80 mg, 0.19 mmol) was reacted with N1,N1,N2-trimethylethane-1,2-diamine (0.030 mL, 0.23 mmol) using a procedure similar to the one described in Example 2.00 to afford N-(2-(dimethylamino)ethyl)-8-(1-(4-fluorophenylamino)ethyl)-N-methyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (15.0 mg, 15.6%) as a white solid. Mass Spectrum: M+H+ 497. NMR Spectrum: (DMSOd6) 1.49 (d, 3H), 1.74 (bs, 3H), 2.01 (bs, 1H), 2.18 (s, 3H), 2.66 (bs, 1.5H), 2.89 (bs, 2H), 3.05 (bs, 1.5H), 3.47 (bs, 1H), 3.50-3.64 (m, 4H), 3.71-3.79 (m, 4H), 4.93-5.01 (m, 1H), 5.59 (s, 1H), 6.29 (bs, 1H), 6.46 (dd, 2H), 6.84 (dd, 2H), 6.54 (d, 1H), 6.73 (d, 1H).

Sources & evidence

ORD record
ord-d008e7e8f4b2491b88f7cbc9b1396d06
Source dataset
uspto-grants-2013_03
Patent number
US08399460B2

Reaction notes

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