Dimethylamine → HCID 69284627, compound

HRID 2225253Notes

Reaction equation

HRID 2225253 reaction equation
Cl[C:2]1[N:11]=[C:10]([NH:12][CH2:13][C:14]([NH:16][C@H:17]2[CH2:22][CH2:21][C@@H:20]([N:23]([CH2:27][CH3:28])[CH:24]([CH3:26])[CH3:25])[CH2:19][C@H:18]2[CH2:29][O:30][CH3:31])=[O:15])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:32])[CH:8]=2)[N:3]=1.[CH3:33][NH:34][CH3:35]>O1CCCC1>[Cl:32][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([N:34]([CH3:35])[CH3:33])[N:11]=[C:10]2[NH:12][CH2:13][C:14]([NH:16][C@H:17]1[CH2:22][CH2:21][C@@H:20]([N:23]([CH2:27][CH3:28])[CH:24]([CH3:25])[CH3:26])[CH2:19][C@H:18]1[CH2:29][O:30][CH3:31])=[O:15]

Participants

4

Reactant 2

HCID 674Dimethylamine2×HCID 86596951HCID 86596951, compound

Product 1

HCID 69284627HCID 69284627, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(2,6-dichloroquinazolin-4-ylamino)-N-((1S,2R,4R)-4-(ethyl(isopropyl)amino)-2-(methoxymethyl)cyclohexyl)acetamide (61 mg) in tetrahydrofuran (2 mL) was treaded with dimethylamine (2 M in tetrahydrofuran, 80 μL) and the mixture was heated at reflux overnight. Additional dimethylamine solution (0.825 mL) was added and heating was continued for 3 more days. Concentration under vacuum and purification by reverse phase HPLC and lyophilization provided the bis-trifluoroacetic acid salt of the title product, 2-(6-chloro-2-(dimethylamino)quinazolin-4-ylamino)-N-((1S,2R,4R)-4-(ethyl(isopropyl)amino)-2-(methoxymethyl)cyclohexyl)acetamide, as a white powder (54 mg). MS found: (M+H)+=491.7.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. temperatureheating
  4. concentrationConcentration
  5. customunder vacuum and purification by reverse phase HPLC and lyophilization

Sources & evidence

ORD record
ord-d3125749318149b890de6059ebc774bb
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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