Acetyl chloride → HCID 46235941, compound

HRID 906029Notes

Reaction equation

[CH3:1][CH:2]1[CH:7]([NH:8][C:9]([NH:11][C:12]2[N:13]=[C:14]3[CH:20]=[CH:19][N:18](COCC[Si](C)(C)C)[C:15]3=[N:16][CH:17]=2)=[O:10])[CH2:6][CH2:5][O:4][CH2:3]1.C(Cl)(=O)C>CO>[CH3:1][C@H:2]1[C@@H:7]([NH:8][C:9]([NH:11][C:12]2[N:13]=[C:14]3[CH:20]=[CH:19][NH:18][C:15]3=[N:16][CH:17]=2)=[O:10])[CH2:6][CH2:5][O:4][CH2:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

1-(3-Methyl-tetrahydro-pyran-4-yl)-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea (0.065 g, 0.16 mmol) was suspended in MeOH and cooled down to 0° C. At that temperature the acetyl chloride (0.4 mL) was added. After the addition was complete the orange solution was allowed to warm up and stirred at 40° C. overnight. The solvent was evaporated and the remaining solid was dried under high vacuum. The orange solid was taken up in MeOH:H2O:Et3N 8:1:1 and stirred at RT for 1 hour. The solvent was evaporated. The remaining off-white solid was absorbed onto SiO2 and purified by SiO2 chromatography (12 g SiO2, DCM/magic (DCM:MeOH:NH4OH 60:10:1) 0-25% magic). Obtained 0.023 g of cis-1-(3-methyl-tetrahydro-pyran-4-yl)-3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-urea as an off-white solid, yield: 52%.

Workup

additionAfter the addition
temperatureto warm up
customThe solvent was evaporated
customthe remaining solid was dried under high vacuum
stirringstirred at RT for 1 hour
customThe solvent was evaporated
customThe remaining off-white solid was absorbed onto SiO2
custompurified by SiO2 chromatography (12 g SiO2, DCM/magic (DCM:MeOH:NH4OH 60:10:1) 0-25% magic)

Sources & evidence

ORD record: ord-eea824d5f3e14e8abd80c9e197682e87
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012974B2

Reaction notes

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