Dimethylcarbamoyl Chloride → HCID 57563242, compound

HRID 1726209Notes

Reaction equation

HRID 1726209 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([C:37]#[N:38])[CH:32]=2)[CH:9]2[CH2:14][CH2:13][N:12]([CH:15]([CH3:29])[CH2:16][CH2:17][NH:18][C:19](=[O:28])[C:20]3[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:21]=3[CH3:27])[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:45][N:46]([CH3:50])[C:47](Cl)=[O:48]>CN(C=O)C>[C:37]([C:33]1[CH:32]=[C:31]([CH:36]=[CH:35][CH:34]=1)[CH2:30][N:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:47]([N:46]([CH3:50])[CH3:45])=[O:48])=[CH:3][CH:4]=1)[CH:9]1[CH2:10][CH2:11][N:12]([CH:15]([CH3:29])[CH2:16][CH2:17][NH:18][C:19](=[O:28])[C:20]2[C:21]([CH3:27])=[CH:22][CH:23]=[CH:24][C:25]=2[CH3:26])[CH2:13][CH2:14]1)#[N:38]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 11430Potassium CarbonateHCID 57563039HCID 57563039, compound

Product 1

HCID 57563242HCID 57563242, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of COMPOUND 142 (61 mg, 0.12 mmol), K2CO3 (50 mg, 0.36 mmol) and dimethylcarbamoyl chloride (23 μL, 0.24 mmol) in DMF (1 mL) was stirred at room temperature for 76 hours to afford COMPOUND 155 as a white solid (53 mg, 76%) following work-up and purification. 1H NMR (CDCl3) δ 0.93-1.17 (m, 2H), 0.99 (d, 3H, J=6.0 Hz), 1.49-1.59 (m, 1H), 1.69-1.78 (m, 3H), 2.14 (t, 1H, J=11.1 Hz), 2.31 (s, 6H), 2.54 (t, 1H, J=10.8 Hz), 2.73-2.85 (m, 3H), 2.98 (s, 6H), 3.27 (t, 1H, J=10.5 Hz), 3.52 (m, 1H), 3.73 (s, 2H), 3.90 (m, 1H), 6.04 (s, 1H), 6.50 (d, 2H, J=8.1 Hz), 6.94-6.99 (m, 3H), 7.09 (d, 2H, J=8.1 Hz), 7.39-7.58 (m, 4H), 8.44 (br s, 1H). 13C NMR (CDCl3) δ 13.81, 19.54, 29.38, 30.74, 31.29, 36.79, 40.28, 43.97, 48.67, 52.61, 57.72, 61.01, 112.75, 115.27, 119.44, 122.87, 127.66, 128.76, 129.49, 130.39, 130.59, 130.76, 131.54, 134.46, 139.03, 142.81, 144.99, 156.69, 170.24. ES-MS m/z 581 (M+H). Anal. Calcd. for C35H44N6O2.0.2CH2Cl2: C, 70.73; H, 7.49; N, 14.06. Found. C, 70.74; H, 7.57; N, 13.74.

Sources & evidence

ORD record
ord-8e62450291534dabb206028e587c575a
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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