Triethylamine → HCID 53466710, compound

HRID 1958312Notes

Reaction equation

HRID 1958312 reaction equation
C(N(CC)CC)C.[CH2:8]([C:10]1[O:14][N:13]=[C:12](C(Cl)=O)[CH:11]=1)C.[C:18]1([C:24]2[N:25]=[C:26]3[N:31]=[C:30]([NH2:32])[CH:29]=[CH:28][N:27]3[CH:33]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH2:34].CC#N>ClCCl>[C:18]1([C:24]2[N:25]=[C:26]3[N:31]=[C:30]([NH:32][C:8]([C:10]4[O:14][N:13]=[CH:12][CH:11]=4)=[O:34])[CH:29]=[CH:28][N:27]3[CH:33]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 18373917Acetonitrile--water (1/1)5×HCID 200727415-Ethyl-1,2-oxazole-3-carbonyl chlorideHCID 508783902-Phenylimidazo[1,2-A]pyrimidin-7-amine

Product 1

HCID 53466710HCID 53466710, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine and 5-ethyl-isoxazole-3-carbonyl chloride were added to a solution of 2-phenyl-imidazo[1,2-a]pyrimidin-7-ylamine (example 1, step 1) in dichloromethane, and the mixture was stirred at RT overnight. The title compound (29 mg, 16%) was isolated from the mixture by preparative HPLC (254 nm, Agilent Zorbax XdB-C18, Run: 7 min, Flow: 30 ml/min, Gradient: 0.0 min: 95/5 H2O/CH3CN; 0.5 min: 95/5 H2O/CH3CN 4.5 min: 5/95 H2O/CH3CN; 6.9 min 5/95 H2O/CH3CN; 7 min 95/5 H2O/CH3CN).

Sources & evidence

ORD record
ord-56ed0518142c414590fadf9e6544b5ad
Source dataset
uspto-grants-2013_04
Patent number
US08410117B2

Reaction notes

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