Acetic Anhydride → HCID 67486976, compound

HRID 1809626Notes

Reaction equation

HRID 1809626 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[N:20]=[CH:19][C:18]([S:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:17][C:16]=3[O:27][C:28]3[C:29]([CH3:34])=[N:30][CH:31]=[CH:32][CH:33]=3)[S:11][N:10]=1)[CH2:2]2.C(N(CC)CC)C.[C:42](OC(=O)C)(=[O:44])[CH3:43]>C(Cl)Cl>[C:42]([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[N:20]=[CH:19][C:18]([S:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:17][C:16]=3[O:27][C:28]3[C:29]([CH3:34])=[N:30][CH:31]=[CH:32][CH:33]=3)[S:11][N:10]=1)[CH2:4]2)(=[O:44])[CH3:43]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 67486978HCID 67486978, compound

Product 1

HCID 67486976HCID 67486976, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-(6-(3-(8-azabicyclo[3.2.1]octan-3-yl)-1,2,4-thiadiazol-5-ylamino)-5-(2-methylpyridin-3-yloxy)pyridin-3-ylthio)acetate (384 mg, 0.770 mmol) was dissolved in CH2Cl2 (7 mL), and triethylamine (16 μL, 1.16 mmol) and acetic anhydride (87.4 μL, 0.924 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 methyl 2-(6-(3-(8-acetyl-8-azabicyclo[3.2.1]octan-3-yl)-1,2,4-thiadiazol-5-ylamino)-5-(2-methylpyridin-3-yloxy)pyridin-3-ylthio)acetate (397 mg, 0.734 mmol, 95.3% yield).

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-c67bd17342ab4cfaa1722e320275772a
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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