Hydrochloric Acid → HCID 67486992, compound

HRID 1809629Notes

Reaction equation

C([O:4][CH2:5][C:6]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][CH:11]([C:16]1[N:20]=[C:19]([NH:21][C:22]3[C:27]([O:28][C:29]4[C:30]([CH3:35])=[N:31][CH:32]=[CH:33][CH:34]=4)=[CH:26][C:25]([S:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=4)=[CH:24][N:23]=3)[S:18][N:17]=1)[CH2:12]2)=[O:7])(=O)C.C([O-])([O-])=O.[K+].[K+].[ClH:49]>CCO>[ClH:49].[OH:4][CH2:5][C:6]([N:8]1[CH:9]2[CH2:15][CH2:14][CH:13]1[CH2:12][CH:11]([C:16]1[N:20]=[C:19]([NH:21][C:22]3[C:27]([O:28][C:29]4[C:30]([CH3:35])=[N:31][CH:32]=[CH:33][CH:34]=4)=[CH:26][C:25]([S:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=4)=[CH:24][N:23]=3)[S:18][N:17]=1)[CH2:10]2)=[O:7]

Participants

Conditions

Temperature: 50 °C

Procedure

2-(3-(5-(3-(2-Methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)-8-azabicyclo[3.2.1]octan-8-yl)-2-oxoethyl acetate (95 mg, 0.157 mmol) was dissolved in EtOH (3 mL) and K2CO3 (excess) was added and heated to 50° C. for 1.5 hr. The reaction was partitioned between CH2Cl2 and saturated aqueous NH4Cl, dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel (15% methanol in EtOAc) to afford 2-hydroxy-1-(3-(5-(3-(2-methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)-8-azabicyclo[3.2.1]octan-8-yl)ethanone hydrochloride (78.2 mg, 0.131 mmol, 83.1% yield) as a solid after HCl salt formation. Mass spectrum (apci) m/z=562.2 (M+H—HCl).

Workup

customThe reaction was partitioned between CH2Cl2 and saturated aqueous NH4Cl
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified on silica gel (15% methanol in EtOAc)

Sources & evidence

ORD record: ord-c829149fdb044caaa6f814f3800a3e12
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362037B2

Reaction notes

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