Tetrahydrofuran → 3,6-Dichloro-5-[4-(1-isopropoxycarbonyl-piperidin-4-yloxyimino)-piperidin-1-yl]-pyrazine-2-carboxylic acid

HRID 2066871Notes

Reaction equation

C[O:2][C:3]([C:5]1[C:10]([Cl:11])=[N:9][C:8]([N:12]2[CH2:17][CH2:16][C:15](=[N:18][O:19][CH:20]3[CH2:25][CH2:24][N:23]([C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]3)[CH2:14][CH2:13]2)=[C:7]([Cl:32])[N:6]=1)=[O:4].C1COCC1.[OH-].[Na+]>Cl>[Cl:11][C:10]1[C:5]([C:3]([OH:4])=[O:2])=[N:6][C:7]([Cl:32])=[C:8]([N:12]2[CH2:13][CH2:14][C:15](=[N:18][O:19][CH:20]3[CH2:21][CH2:22][N:23]([C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27])[CH2:24][CH2:25]3)[CH2:16][CH2:17]2)[N:9]=1

Participants

Conditions

Temperature: 50 °C

Procedure

The crude 56b obtained in the previous step was taken up with THF (1 mL) and 1N NaOH (1 mL) and heated to 50° C. for 3 h. The mixture was cooled, diluted with 5 mL of 1N HCl and extracted with EtOAc (3×5 mL). The combined extracts were dried and concentrate to afford 0.13 g of crude 56c. 25 mg of this material was purified by preparative HPLC to afford 56c: LC-MS 474.7 (MH+).

Workup

temperatureThe mixture was cooled
extractionextracted with EtOAc (3×5 mL)
customThe combined extracts were dried
concentrationconcentrate

Sources & evidence

ORD record: ord-8ec9111020314120bbd02763cb88bce1
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293729B2

Reaction notes

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