Triethylamine → HCID 58006260, compound

HRID 215932Notes

Reaction equation

HRID 215932 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[C:4]=1[CH2:5][N:6]1[CH2:9][CH:8]([NH2:10])[CH2:7]1.[Cl:18][C:19]1[N:28]=[C:27](Cl)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1.CCN(CC)CC>C1COCC1.CN(C1C=CN=CC=1)C>[Cl:18][C:19]1[N:28]=[C:27]([NH:10][CH:8]2[CH2:9][N:6]([CH2:5][C:4]3[C:11]([O:15][CH3:16])=[CH:12][CH:13]=[CH:14][C:3]=3[N:2]([CH3:17])[CH3:1])[CH2:7]2)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2528862,4-DichloroquinazolineHCID 58006214HCID 58006214, compound

Product 1

HCID 58006260HCID 58006260, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Compound 168 (0.22 g, 0.92 mmol) in THF (10.0 mL) at 0° C. was added 2,4-dichloroquinazoline (0.22 g, 1.10 mmol), followed by Et3N (0.65 mL, 4.60 mmol) and DMAP (catalytic amount), and the reaction was allowed to warm up slowly to ambient temperature and stirred for 18 h, then quenched with 7N NH3 in MeOH. The solvent was removed, and the residue was purified by preparative thin layer chromatography with 7N NH3 in MeOH (2%), hexanes (8%) and CH2Cl2 (90%) to afford the compound EE as a yellow solid.

Workup

  1. customquenched with 7N NH3 in MeOH
  2. customThe solvent was removed
  3. customthe residue was purified by preparative thin layer chromatography with 7N NH3 in MeOH (2%), hexanes (8%) and CH2Cl2 (90%)
  4. customto afford the compound EE as a yellow solid

Sources & evidence

ORD record
ord-a7a737f17868401383a792e07f7b951d
Source dataset
uspto-grants-2012_06
Patent number
US08193203B2

Reaction notes

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