Acetyl chloride → (2S,4S)-4-(8-chloro-2-(4-isopropylthiazol-2-yl)-7-methoxyquinolin-4-yloxy)-N-(hex-5-enyl)-N-methylpyrrolidine-2-carboxamide hydrochloride

HRID 420092Notes

Reaction equation

[Cl:1][C:2]1[C:3]([O:43][CH3:44])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[S:13][CH:14]=[C:15]([CH:17]([CH3:19])[CH3:18])[N:16]=1)[CH:8]=[C:7]2[O:20][C@@H:21]1[CH2:25][N:24](C(OC(C)(C)C)=O)[C@H:23]([C:33](=[O:42])[N:34]([CH2:36][CH2:37][CH2:38][CH2:39][CH:40]=[CH2:41])[CH3:35])[CH2:22]1.C(Cl)(=O)C>CO>[ClH:1].[Cl:1][C:2]1[C:3]([O:43][CH3:44])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[S:13][CH:14]=[C:15]([CH:17]([CH3:19])[CH3:18])[N:16]=1)[CH:8]=[C:7]2[O:20][C@@H:21]1[CH2:25][NH:24][C@H:23]([C:33]([N:34]([CH2:36][CH2:37][CH2:38][CH2:39][CH:40]=[CH2:41])[CH3:35])=[O:42])[CH2:22]1

Participants

Conditions

Temperature: 40 °C

Procedure

Compound 134 (20.37 g) was suspended in anhydrous methanol (120 mL) under argon at room temperature. Separately acetyl chloride (3 eq.) was added to anhydrous methanol (70 mL) at 10-20° C. This solution was added to the compound 134 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 100 mL of anhydrous dichloromethane. The product was then dried in a vacuum oven at 40-45° C. Compound 135 (19.81 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 135 (19.81 g) was recovered as a yellow foam in quantitative yield and 100% purity (HPLC)

Sources & evidence

ORD record: ord-f097c5c239544049a1b4429a3a55b870
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093379B2

Reaction notes

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