Dimethylcarbamoyl Chloride → HCID 66679239, compound

HRID 1626691Notes

Reaction equation

HRID 1626691 reaction equation
[CH:1]1([NH:4][C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:15]=[C:16]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][C@@H:25]4[CH3:30])[C:17]4[CH2:23][CH2:22][NH:21][CH2:20][C:18]=4[N:19]=3)=[C:10]([F:31])[CH:9]=2)=[O:6])[CH2:3][CH2:2]1.CCN(CC)CC.[CH3:39][N:40]([CH3:44])[C:41](Cl)=[O:42]>CN(C=O)C>[CH:1]1([NH:4][C:5](=[O:6])[NH:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:15]=[C:16]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][C@@H:25]4[CH3:30])[C:17]4[CH2:23][CH2:22][N:21]([C:41]([N:40]([CH3:44])[CH3:39])=[O:42])[CH2:20][C:18]=4[N:19]=3)=[C:10]([F:31])[CH:9]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 66679238HCID 66679238, compound

Product 1

HCID 66679239HCID 66679239, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

To a stirring solution of (S)-1-cyclopropyl-3-(3-fluoro-4-(4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (example 163) (99 mg, 0.23 mmol) and NEt3 (35 μL, 0.25 mmol) in DMF (2 ml) was added dimethylcarbamoyl chloride (29 μL, 0.25 mmol). Reaction mixture was stirred at room temperature (20° C.) overnight before being concentrated in vacuo and purified by prep. HPLC at high pH to afford a white solid (42 mg, 37%).

Workup

  1. customReaction mixture
  2. concentrationbefore being concentrated in vacuo
  3. custompurified by prep

Sources & evidence

ORD record
ord-9c4acb5c3cde4062a9c7dae1196496f8
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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