Dimethylcarbamoyl Chloride → HCID 57563072, compound

HRID 1726199Notes

Reaction equation

HRID 1726199 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:39]=[CH:40][CH:41]=1)[CH2:6][N:7]([CH:18]1[CH2:23][CH2:22][N:21]([CH:24]([CH3:38])[CH2:25][CH2:26][NH:27][C:28]([C:30]2[C:31]([CH3:37])=[N:32][CH:33]=[N:34][C:35]=2[CH3:36])=[O:29])[CH2:20][CH2:19]1)[C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15](=[O:17])C)=[CH:10][CH:9]=1)#[N:2].C([O-])([O-])=O.[K+].[K+].[CH3:48][N:49](C)[C:50](Cl)=O>CN(C=O)C>[C:1]([C:3]1[CH:4]=[C:5]([CH:39]=[CH:40][CH:41]=1)[CH2:6][N:7]([CH:18]1[CH2:23][CH2:22][N:21]([CH:24]([CH3:38])[CH2:25][CH2:26][NH:27][C:28]([C:30]2[C:35]([CH3:36])=[N:34][CH:33]=[N:32][C:31]=2[CH3:37])=[O:29])[CH2:20][CH2:19]1)[C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15](=[O:17])[N:49]([CH3:50])[CH3:48])=[CH:10][CH:9]=1)#[N:2]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 11430Potassium CarbonateHCID 57563064HCID 57563064, compound

Product 1

HCID 57563072HCID 57563072, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of COMPOUND 138 (43 mg, 0.084 mmol) in DMF (1 mL) were added K2CO3 (38 mg, 0.27 mmol) followed by dimethylcarbamoyl chloride (15 μL, 0.16 mmol) and the mixture was stirred at room temperature overnight to afford COMPOUND 146 as a white solid (27 mg, 53%) following work-up and purification. 1H NMR (CDCl3) δ 0.86-1.13 (m, 2H), 1.02 (d, 3H, J=6.6 Hz), 1.52-1.59 (m, 1H), 1.75-1.79 (m, 3H), 2.16 (t, 1H, J=11.4 Hz), 2.52 (s, 6H), 2.57 (t, 1H, J=10.5 Hz), 2.73-2.88 (m, 3H), 2.98 (s, 3H), 3.05 (s, 3H), 3.28-3.36 (m, 1H), 3.53-3.60 (m, 1H), 3.83-3.87 (m, 1H), 3.87 (s, 2H), 6.53 (d, 2H, J=9.0 Hz), 6.88 (d, 2H, J=9.0 Hz), 7.40-7.45 (m, 1H), 7.50-7.56 (m, 3H), 8.65-8.66 (m, 1H), 8.84 (s, 1H). 13C NMR (CDCl3) δ 14.72, 23.24, 30.49, 31.68, 32.01, 37.66, 37.95, 41.32, 44.90, 49.82, 53.32, 58.14, 61.53, 113.83, 115.91, 120.24, 123.71, 130.55, 131.32, 131.88, 132.15, 132.37, 143.13, 144.63, 146.97, 156.73, 158.83, 164.36, 167.61. ES-MS m/z 584 (M+H). Anal. Calcd. for C33H41N7O3.1.4H2O: C, 65.09; H, 7.25; N, 16.10. Found. C, 65.27; H, 6.88; N, 15.76.

Sources & evidence

ORD record
ord-4dbe40947eb6472682942ca35e48e6ea
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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