Acetic Anhydride → HCID 57585012, compound

HRID 2077596Notes

Reaction equation

HRID 2077596 reaction equation
[CH:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:10]1[N:15]=[C:14]([C:16]3[CH:25]=[CH:24][C:19]4[N:20]=[C:21]([NH2:23])[S:22][C:18]=4[CH:17]=3)[CH:13]=[N:12][CH:11]=1)[CH2:2]2.[C:26](OC(=O)C)(=[O:28])[CH3:27].[Al]>N1C=CC=CC=1>[CH:5]12[CH2:8][CH2:9][CH:1]([CH2:7][CH2:6]1)[CH2:2][N:3]([C:10]1[N:15]=[C:14]([C:16]3[CH:25]=[CH:24][C:19]4[N:20]=[C:21]([NH:23][C:26](=[O:28])[CH3:27])[S:22][C:18]=4[CH:17]=3)[CH:13]=[N:12][CH:11]=1)[CH2:4]2

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 5359268AluminumHCID 86628000HCID 86628000, compound

Product 1

HCID 57585012HCID 57585012, compoundYield 2.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

6-(6-(3-aza-bicyclo[3.2.2]nonan-3-yl)pyrazin-2-yl)benzo[d]thiazol-2-amine was dissolved in 0.5 mL dry pyridine in a Biotage high recovery microwave vessel with a stirbar and treated with acetic anhydride (0.020 ml, 0.22 mmol). The vessel was swept with Ar, sealed and place into a 60° C. aluminum heat transfer block. The reaction was stirred for 4 h and cooled. The solution was treated with Si Carbonate (0.31 g, 0.22 mmol) (loading=0.69 mmol g−1), and the slurry was stirred at room temperature for 30 minutes. The slurry was filtered, and the silica was washed with dry pyridine (3 mL). The solvent was removed in vacuo to afford N-(6-(6-(3-aza-bicyclo[3.2.2]nonan-3-yl)pyrazin-2-yl)benzo[d]thiazol-2-yl)acetamide (0.0024 g, 2.8% yield). 1H NMR (400 MHz, Pyr) δ ppm 1.22-1.41 (m, 8H) 1.76 (br. s., 2H) 2.06 (s, 3H) 3.57 (d, J=4.21 Hz, 4H) 7.85 (d, J=8.51 Hz, 1H) 8.12 (dd, J=8.41, 1.86 Hz, 1H) 8.13 (s, 1H) 8.48 (s, 1H) 8.71 (d, J=1.66 Hz, 1H) 13.58 (br. s., 1H). HPLC-MS: retention time=2.18 min (95%@215 nm; 97% @254 nm; m/z=394.2, calculated for C21H23N5OS+H+=394.2).

Workup

  1. customsealed
  2. temperaturecooled
  3. stirringthe slurry was stirred at room temperature for 30 minutes
  4. filtrationThe slurry was filtered
  5. washthe silica was washed with dry pyridine (3 mL)
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-fc00f758c17442dc9ac27011d8f682cb
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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