Acetyl chloride → (2S,4S)-N-(hex-5-enyl)-4-(7-methoxy-8-methyl-2-(4-(trifluoromethyl)thiazol-2-yl)quinolin-4-yloxy)-N-methylpyrrolidine-2-carboxamide

HRID 1675447Notes

Reaction equation

[CH2:1]([N:7]([CH3:45])[C:8]([C@@H:10]1[CH2:14][C@H:13]([O:15][C:16]2[C:25]3[C:20](=[C:21]([CH3:28])[C:22]([O:26][CH3:27])=[CH:23][CH:24]=3)[N:19]=[C:18]([C:29]3[S:30][CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[N:33]=3)[CH:17]=2)[CH2:12][N:11]1C(OC(C)(C)C)=O)=[O:9])[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].C(Cl)(=O)C>CO>[CH2:1]([N:7]([CH3:45])[C:8]([C@@H:10]1[CH2:14][C@H:13]([O:15][C:16]2[C:25]3[C:20](=[C:21]([CH3:28])[C:22]([O:26][CH3:27])=[CH:23][CH:24]=3)[N:19]=[C:18]([C:29]3[S:30][CH:31]=[C:32]([C:34]([F:35])([F:36])[F:37])[N:33]=3)[CH:17]=2)[CH2:12][NH:11]1)=[O:9])[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6]

Participants

Conditions

Temperature: 40 °C

Procedure

Compound 126 (19.92 g) was suspended in anhydrous methanol (120 mL) under argon at room temperature. Separately acetyl chloride (3 eq.) was added to anhydrous methanol (60 mL) at 10-20° C. This solution was added to the compound 126 solution at 5° C. The reaction mixture was heated at 40° C. for 3-4 hrs. After the completion of the reaction, the reaction mixture was concentrated under vacuum and then co-evaporated with 200 mL of anhydrous dichloromethane. The product was then dried in a vacuum oven at 40-45° C. Compound 127 (18.35 g) was recovered as a yellow foam in quantitative yield and 100% purity (HPLC).

Workup

customAfter the completion of the reaction
concentrationthe reaction mixture was concentrated under vacuum
customThe product was then dried in a vacuum oven at 40-45° C
customCompound 127 (18.35 g) was recovered as a yellow foam in quantitative yield and 100% purity (HPLC)

Sources & evidence

ORD record: ord-ccb6e5e412274d469d27cbce927a0f40
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003659B2

Reaction notes

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