Citric Acid → HCID 86643333, compound

HRID 1948288Notes

Reaction equation

[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][C:20]([C:23]([O:25]C)=[O:24])=[CH:21][N:22]=2)[CH2:14][C@H:13]1[O:27][CH3:28])=[O:10].[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][C:20]([C:23]([OH:25])=[O:24])=[CH:21][N:22]=2)[CH2:14][C@H:13]1[O:27][CH3:28])=[O:10]

Participants

Conditions

Temperature: 50 °C

Procedure

Cis(±)methyl 2-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-1,3-thiazole-5-carboxylate (Example 1; 200 mg) was dissolved in THF (50 ml). 2N LiOH (100 ml) was added and the mixture was heated at 50° C. for 18 h. The reaction mixture was cooled to ambient and acidified with 20% aqueous citric acid. The aqueous phase was extracted with EtOAc and the organic phase was washed with water, brine, dried over Na2SO4. The organic phase was concentrated in vacuo and triturated with diethyl ether to give the title compound as an off white solid. (164 mg). MS (ES) MH+: 433, 431 for C16H18Cl2N4O4S; NMR: 1.87 (m, 2H), 2.28 (s, 3H), 3.32 (m, 6H), 3.63 (s, 1H), 3.87 (m, 1H), 4.45 (m, 2H), 7.04 (d, 1H), 7.90 (s, 1H), 11.97 (s, 1H), 12.30 (s, 1H).

Workup

temperatureThe reaction mixture was cooled to ambient and
extractionThe aqueous phase was extracted with EtOAc
washthe organic phase was washed with water, brine
dry with materialdried over Na2SO4
concentrationThe organic phase was concentrated in vacuo
customtriturated with diethyl ether

Sources & evidence

ORD record: ord-ece02c718a0d47d68c025534f87369c1
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399489B2

Reaction notes

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