Hydrochloric Acid → HCID 69287995, compound

HRID 2375794Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To 34 mg (0.06 mmol) of 3-[1-[5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-(1-isopropyl-piperidin-4-ylcarbamoyl)-2,4-dimethyl-1H-pyrrol-3-yl]-propionic acid methyl ester in MeOH (4 mL) 1 M aqueous LiOH-solution (0.3 mL) was added and the resulting mixture was stirred at 60° C. for 5 h. The mixture was acidified by the addition of a 1 M HCl-solution (pH 5) and concentrated under reduced pressure. Final purification by preparative HPLC(CH3CN/H2O gradient+0.05% formic acid) gave pure 3-[1-[5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-(1-isopropyl-piperidin-4-ylcarbamoyl)-2,4-dimethyl-1H-pyrrol-3-yl]-propionic acid as a colorless amorphous material. The product was obtained as its hydroformiate (11 mg). MS (ESI+): m/e=534 [M+H]+, chloro pattern.

Workup

concentrationconcentrated under reduced pressure
customFinal purification by preparative HPLC(CH3CN/H2O gradient+0.05% formic acid)

Sources & evidence

ORD record: ord-12a4bb717a044a418e9e0fbf3d904e1e
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465806B2

Reaction notes

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