Dimethylamine → HCID 58091559, compound

HRID 1874010Notes

Reaction equation

HRID 1874010 reaction equation
Cl[C:2]1[N:7]=[C:6]2[O:8][C:9]3[N:26]=[C:25]([C:27]4[CH:37]=[CH:36][C:30]([C:31]([N:33]([CH3:35])[CH3:34])=[O:32])=[CH:29][CH:28]=4)[CH:24]=[CH:23][C:10]=3[CH:11]([C:12]([CH3:22])([CH3:21])[C:13](=[O:20])[NH:14][C:15]3[S:16][CH:17]=[N:18][N:19]=3)[C:5]2=[CH:4][CH:3]=1.[CH3:38][NH:39][CH3:40]>CO>[CH3:38][N:39]([CH3:40])[C:2]1[N:7]=[C:6]2[O:8][C:9]3[N:26]=[C:25]([C:27]4[CH:37]=[CH:36][C:30]([C:31]([N:33]([CH3:35])[CH3:34])=[O:32])=[CH:29][CH:28]=4)[CH:24]=[CH:23][C:10]=3[CH:11]([C:12]([CH3:22])([CH3:21])[C:13](=[O:20])[NH:14][C:15]3[S:16][CH:17]=[N:18][N:19]=3)[C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 58091600HCID 58091600, compound

Product 1

HCID 58091559HCID 58091559, compoundYield 103.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
220 °C

Procedure

A solution of the ester from Step 3 of Example 54 (39 mg, 0.084 mmol), 40% aqueous dimethylamine (1 mL, 7.90 mmol) in MeOH (0.5 mL) was attempted to heat to 220° C. under microwave, but stopped due to high pressure (>19 psi). The mixture was then heated to ˜150° C. under microwave for 1 h. Purification by reverse phase HPLC (Sunfire S10 30×250 mm column, 55 to 85% solvent B gradient) gave the expected product (47.3 mg, 70% yield). MS (ES+) m/z: 461 (M+H); LC retention time: 3.67 min (analytical HPLC Method A).

Workup

  1. temperatureThe mixture was then heated to ˜150° C. under microwave for 1 h
  2. customPurification by reverse phase HPLC (Sunfire S10 30×250 mm column, 55 to 85% solvent B gradient)

Sources & evidence

ORD record
ord-2ba0ec55798c463a9b9a1feb6d6b555b
Source dataset
uspto-grants-2012_11
Patent number
US08304539B2

Reaction notes

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