Diisopropylethylamine → HCID 86596951, compound

HRID 2225252Notes

Reaction equation

HRID 2225252 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:13])[CH:8]=2)[N:3]=1.[NH2:14][CH2:15][C:16]([NH:18][C@H:19]1[CH2:24][CH2:23][C@@H:22]([N:25]([CH2:29][CH3:30])[CH:26]([CH3:28])[CH3:27])[CH2:21][C@H:20]1[CH2:31][O:32][CH3:33])=[O:17].C(N(C(C)C)CC)(C)C>O1CCCC1>[Cl:1][C:2]1[N:11]=[C:10]([NH:14][CH2:15][C:16]([NH:18][C@H:19]2[CH2:24][CH2:23][C@@H:22]([N:25]([CH2:29][CH3:30])[CH:26]([CH3:28])[CH3:27])[CH2:21][C@H:20]2[CH2:31][O:32][CH3:33])=[O:17])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:13])[CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 104215102,4,6-TrichloroquinazolineHCID 69287222HCID 69287222, compound

Product 1

HCID 86596951HCID 86596951, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,4,6-trichloroquinazoline (103 mg) and the bis-trifluoroacetic acid salt of 2-amino-N-((1S,2R,4R)-4-(ethyl(isopropyl)amino)-2-(methoxymethyl)cyclohexyl)acetamide (152 mg) in tetrahydrofuran (3 mL) was treated with diisopropylethylamine (0.31 mL) and the mixture was stirred overnight at rt. The mixture was concentrated and purified by reverse phase HPLC and lyophilization to provide the bis-trifluoroacetic acid salt of the title compound, 2-(2,6-dichloroquinazolin-4-ylamino)-N-((1S,2R,4R)-4-(ethyl(isopropyl)amino)-2-(methoxymethyl)cyclohexyl)acetamide, as a white powder (79 mg). MS found: (M+H)+=482.2.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by reverse phase HPLC and lyophilization

Sources & evidence

ORD record
ord-784879a3cc7a459680430cdd132dde96
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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