Hydrochloric Acid → HCID 68711156, compound

HRID 1809632Notes

Reaction equation

HRID 1809632 reaction equation
[CH:1]12[NH:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][CH:3]([C:9]1[N:13]=[C:12]([NH:14][C:15]3[C:20]([O:21][C:22]4[C:23]([CH3:28])=[N:24][CH:25]=[CH:26][CH:27]=4)=[CH:19][C:18]([S:29][CH2:30][CH2:31][O:32][CH3:33])=[CH:17][N:16]=3)[S:11][N:10]=1)[CH2:2]2.C(N(CC)CC)C.[C:41](OC(=O)C)(=[O:43])[CH3:42].[ClH:48]>C1COCC1>[ClH:48].[CH3:33][O:32][CH2:31][CH2:30][S:29][C:18]1[CH:19]=[C:20]([O:21][C:22]2[C:23]([CH3:28])=[N:24][CH:25]=[CH:26][CH:27]=2)[C:15]([NH:14][C:12]2[S:11][N:10]=[C:9]([CH:3]3[CH2:2][CH:1]4[N:8]([C:41](=[O:43])[CH3:42])[CH:5]([CH2:6][CH2:7]4)[CH2:4]3)[N:13]=2)=[N:16][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 67487773HCID 67487773, compound

Product 1

HCID 68711156HCID 68711156, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(8-Azabicyclo[3.2.1]octan-3-yl)-N-(5-(2-methoxyethylthio)-3-(2-methylpyridin-3-yloxy)pyridin-2-yl)-1,2,4-thiadiazol-5-amine (96 mg, 0.198 mmol) was dissolved in THF (4 mL) and triethylamine (55.2 μL, 0.396 mmol) and acetic anhydride (22.5 μL, 0.238 mmol) were added. The reaction was stirred at ambient temperature for 5 minutes. The reaction was partitioned between saturated aqueous NaHCO3 and CH2Cl2, dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel (20% methanol in EtOAc) to afford 1-(3-(5-(5-(2-methoxyethylthio)-3-(2-methylpyridin-3-yloxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)-8-azabicyclo[3.2.1]octan-8-yl)ethanone hydrochloride (91.6 mg, 0.163 mmol, 82.1% yield) as a solid after HCl salt formation. Mass spectrum (apci) m/z=527.2 (M+H—HCl).

Workup

  1. customThe reaction was partitioned between saturated aqueous NaHCO3 and CH2Cl2
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified on silica gel (20% methanol in EtOAc)

Sources & evidence

ORD record
ord-03cda403fb064de0bf2f393fd15418ca
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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