Dimethylcarbamoyl Chloride → HCID 57563007, compound

HRID 1726198Notes

Reaction equation

HRID 1726198 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:36]=[CH:37][CH:38]=1)[CH2:6][N:7]([C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)[CH:8]1[CH2:13][CH2:12][N:11]([CH:14]([CH3:28])[CH2:15][CH2:16][NH:17][C:18](=[O:27])[C:19]2[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:26])[CH2:10][CH2:9]1)#[N:2].C([O-])([O-])=O.[K+].[K+].[CH3:45][N:46]([CH3:50])[C:47](Cl)=[O:48]>CN(C=O)C>[C:1]([C:3]1[CH:4]=[C:5]([CH:36]=[CH:37][CH:38]=1)[CH2:6][N:7]([CH:8]1[CH2:13][CH2:12][N:11]([CH:14]([CH3:28])[CH2:15][CH2:16][NH:17][C:18](=[O:27])[C:19]2[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:26])[CH2:10][CH2:9]1)[C:29]1[CH:34]=[CH:33][C:32]([O:35][C:47](=[O:48])[N:46]([CH3:50])[CH3:45])=[CH:31][CH:30]=1)#[N:2]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 11430Potassium CarbonateHCID 57563088HCID 57563088, compound

Product 1

HCID 57563007HCID 57563007, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of COMPOUND 117 (42 mg, 0.082 mmol) in DMF (1 mL) were added K2CO3 (36 mg, 0.26 mmol) followed by dimethylcarbamoyl chloride (15 μL, 0.16 mmol) and the mixture was stirred at room temperature overnight to afford COMPOUND 145 as a white solid (41 mg, 84%) following work-up and purification. 1H NMR (CDCl3) δ 0.93-1.13 (m, 2H), 0.99 (d, 3H, J=6.3 Hz), 1.50-1.58 (m, 1H), 1.70-1.81 (m, 3H), 2.14 (t, 1H, J=11.4 Hz), 2.31 (s, 6H), 2.54 (t, 1H, J=12.0 Hz), 2.73-3.05 (m, 9H), 3.23-3.28 (m, 1H), 3.51-5.56 (m, 1H), 3.75 (s, 2H), 3.87-3.93 (m, 1H), 6.50 (d, 2H, J=7.8 Hz), 6.86 (d, 2H, J=8.1 Hz), 6.93-7.00 (m, 3H), 7.42-7.50 (m, 4H), 8.42-8.44 (m, 1H). 13C NMR (CDCl3) δ 13.80, 19.53, 29.34, 30.75, 31.32, 36.75, 36.87, 37.04, 38.99, 40.24, 43.97, 48.81, 52.57, 57.43, 60.97, 112.84, 114.79, 119.36, 122.74, 127.68, 128.77, 129.57, 130.45, 130.83, 131.40, 134.47, 139.04, 142.64, 143.47, 146.18, 155.88, 162.90, 170.23. ES-MS m/z 582 (M+H). Anal. Calcd. for C35H43N5O3.1.0H2O: C, 70.09; H, 7.56; N, 11.68. Found. C, 70.35; H, 7.56; N, 11.95.

Sources & evidence

ORD record
ord-629c6666dbaa43daa080852bed5d5f54
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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