Methoxyacetyl chloride → HCID 20756588, compound

HRID 230382Notes

Reaction equation

HRID 230382 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]3[C@H:14]([CH2:15][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[NH:13][CH:12]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:11][N:10]3[CH:28]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:29][O:30][CH2:31][C:32](Cl)=[O:33]>C(Cl)(Cl)Cl>[CH3:29][O:30][CH2:31][C:32]([N:13]1[CH:12]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:11][N:10]2[CH:28]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=[C:9]2[C@@H:14]1[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:33]

Participants

4

Reactant 2

HCID 96623Methoxyacetyl chlorideHCID 20756587HCID 20756587, compound

Product 1

HCID 20756588HCID 20756588, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 5,6,7,8-tetrahydro-2,6-diphenyl-8(S)-phenylmethyl-imidazo[1,2-a]pyrazine (29 mg) in chloroform were successively added morpholinomethylpolystyrene resin (Novabiochem, loading=3.51 mmol/g, 50 mg, 2 eq) and methoxyacetylchloride (10 mL, 1.3 eq). After about 3 hours of stirring at about 20° C. chloroform was added to the mixture followed by aminomethylpolystyrene resin (Novabiochem, loading=1.2 mmol/g, 132 mg, 2 eq). The reaction mixture was stirred for another 2 hours and then filtered. The filtrate was concentrated under reduced pressure to afford 23 mg of the title compound (yield=68%). NMR (1H, 100 MHz, CDCl3): 7.9-7.0 (m, 16H, arom, H), 6.6 (m, 1H, H1), 5.3 (m, 1H, H1), 4.6 (dd, 1H, 2J=13 Hz, H5), 4.35 (dd, 1H, 2J=13 Hz, 3J=5 Hz, H5′), 3.7-2.9 (m, 5H, CH2Ph, OCH3).

Workup

  1. additionwas added to the mixture
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ba62933f95804353a84d1d44cd7bdc4f
Source dataset
uspto-grants-2009_07
Patent number
US07566734B2

Reaction notes

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