Trifluoroacetic acid → HCID 135507290, compound

HRID 719900Notes

Reaction equation

C([O:5][NH:6][C:7]([C:9]1[CH:14]=[N:13][C:12]([NH:15][C:16](=[O:35])[C@@H:17]([C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[C:26]([Cl:34])[CH:25]=2)[CH2:18][CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:11][N:10]=1)=[O:8])(C)(C)C.[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39]>C(Cl)Cl>[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39].[OH2:5].[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39].[OH:5][NH:6][C:7]([C:9]1[CH:14]=[N:13][C:12]([NH:15][C:16](=[O:35])[C@@H:17]([C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:31])=[O:32])=[C:26]([Cl:34])[CH:25]=2)[CH2:18][CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:11][N:10]=1)=[O:8]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 5-[2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionylamino]-pyrazine-2-carboxylic acid tert-butoxy-amide (318.3 mg, 0.609 mol) in methylene chloride (2.3 mL) was treated with trifluoroacetic acid (4.6 mL) and stirred at 25° C. overnight, then at 40° C. for 10–11 h, followed by stirring again at 25° C. overnight. The reaction solution was then concentrated in vacuo. Reverse phase high-performance liquid chromatography (Rainin Dynamax system, 60 Å C-18 column, l=214 nm, 50 mL/min of 50–100% acetonitrile with 0.1% trifluoroacetic acid/water with 0.1% trifluoroacetic acid over 55 min) afforded 5-[2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionylamino]-pyrazine-2-carboxylic acid hydroxyamide (90.0 mg, 32%) as a pink foam: mp 134–139° C. (foam to gel); (ES)+-HRMS m/e calcd for C20H23ClN4O5S (M+H)+ 467.1151, found 467.1155.

Workup

waitat 40° C. for 10–11 h
stirringby stirring again at 25° C. overnight
concentrationThe reaction solution was then concentrated in vacuo

Sources & evidence

ORD record: ord-194afbc037e94f28996166e52c7111f8
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07132425B2

Reaction notes

Loading…