Hydrochloric Acid → HCID 67487736, compound

HRID 1809623Notes

Reaction equation

HRID 1809623 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][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=4)=[CH:17][N:16]=3)[S:11][N:10]=1)[CH2:2]2.C(N(CC)CC)C.[C:43](OC(=O)C)(=[O:45])[CH3:44].[ClH:50]>C(Cl)Cl>[ClH:50].[CH3:28][C:23]1[C:22]([O:21][C:20]2[C:15]([NH:14][C:12]3[S:11][N:10]=[C:9]([CH:3]4[CH2:4][CH:5]5[N:8]([C:43](=[O:45])[CH3:44])[CH:1]([CH2:7][CH2:6]5)[CH2:2]4)[N:13]=3)=[N:16][CH:17]=[C:18]([S:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=3)[CH:19]=2)=[CH:27][CH:26]=[CH:25][N:24]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 67487214HCID 67487214, compound

Product 1

HCID 67487736HCID 67487736, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(8-azabicyclo[3.2.1]octan-3-yl)-N-(3-(2-methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-yl)-1,2,4-thiadiazol-5-amine (100 mg, 0.199 mmol) was dissolved in CH2Cl2 (3 mL) and triethylamine (41.5 μL, 0.298 mmol) and acetic anhydride (22.5 μL, 0.238 mmol) were added and the reaction stirred for 5 minutes. The reaction was partitioned between saturated aqueous NaHCO3 and CH2Cl2, dried over sodium sulfate, filtered, concentrated and purified on silica gel (10% methanol in EtOAc) to afford 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 (95.2 mg, 0.164 mmol, 82.4% yield) as a solid after HCl salt formation. Mass spectrum (apci) m/z=546.0 (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. custompurified on silica gel (10% methanol in EtOAc)

Sources & evidence

ORD record
ord-c6759183c9c94bd7959e0eb14d4a15d4
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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