Triethylamine → HCID 67487819, compound

HRID 1809628Notes

Reaction equation

HRID 1809628 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]([O:46][CH2:47][C:48](Cl)=[O:49])(=[O:45])[CH3:44]>C(Cl)Cl>[C:43]([O:46][CH2:47][C:48]([N:8]1[CH:5]2[CH2:6][CH2:7][CH:1]1[CH2:2][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)[CH2:4]2)=[O:49])(=[O:45])[CH3:44]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 26297Acetoxyacetyl chlorideHCID 67487214HCID 67487214, compound

Product 1

HCID 67487819HCID 67487819, compoundYield 100%

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 (80 mg, 0.159 mmol; prepared in Example 174, step C) was dissolved in CH2Cl2, and triethylamine (88.6 μL, 0.635 mmol) and 2-chloro-2-oxoethyl acetate (25.6 μL, 0.238 mmol) were added. The reaction was stirred at ambient temperature for 5 minutes. The reaction was partitioned between CH2Cl2 and saturated aqueous NaHCO3, dried over sodium sulfate, filtered and concentrated to afford 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 (95.9 mg, 0.159 mmol, 100% yield) as a crude foam.

Workup

  1. customThe reaction was partitioned between CH2Cl2 and saturated aqueous NaHCO3
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2f725d7507934c0396d8c1ca526cdd42
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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