Acetyl chloride → N-(2-(2-(3-(benzyloxy)pyridin-2-ylamino)thiazol-4-yl)ethyl)acetamide hydrochloride

HRID 1426173Notes

Reaction equation

HRID 1426173 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[N:5]=[C:6]([NH:9][C:10]2[C:15]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:14][CH:13]=[CH:12][N:11]=2)[S:7][CH:8]=1.C(N(CC)CC)C.[C:31]([Cl:34])(=[O:33])[CH3:32]>CN(C=O)C>[ClH:34].[CH2:17]([O:16][C:15]1[C:10]([NH:9][C:6]2[S:7][CH:8]=[C:4]([CH2:3][CH2:2][NH:1][C:31](=[O:33])[CH3:32])[N:5]=2)=[N:11][CH:12]=[CH:13][CH:14]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 866397044-(2-aminoethyl)-N-(3-(benzyloxy)pyridin-2-yl)thiazol-2-amine

Product 1

HCID 86639705N-(2-(2-(3-(benzyloxy)pyridin-2-ylamino)thiazol-4-yl)ethyl)acetamide hydrochlorideYield 46.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Crude 4-(2-aminoethyl)-N-(3-(benzyloxy)pyridin-2-yl)thiazol-2-amine (0.50 g, 1.53 mmol) was dissolved in DMF (20 mL), and triethylamine (0.854 ml, 6.13 mmol) was added, followed by the addition of acetyl chloride (0.240 g, 3.06 mmol). The reaction mixture was stirred for 2 hours, then partitioned between ethyl acetate and water. The organic layer was washed with water and brine, dried, and concentrated. The residue was dissolved in THF (10 mL) and 1N HCl in ether (2 mL) was added. The mixture was diluted in ether (15 mL) and triturated for 15 minutes, and the solids were filtered, washed with ether and hexanes, and dried to afford the title compound (0.290 g, 46.8% yield) as a light yellow powder. 1H NMR (DMSO-d6) δ 1.80 (s, 3H), 2.80 (m, 2H), 3.37 (m, 2H), 5.34 (s, 2H), 6.96 (s, 1H), 7.15 (m, 1H), 7.32-7.43 (m, 3H), 7.57-7.66 (m, 3H), 8.00 (d, 1H), 8.05 (t, 1H), 8.20 (bs, 1H), 11.35 (bs, 1H).

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic layer was washed with water and brine
  3. customdried
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in THF (10 mL)
  6. addition1N HCl in ether (2 mL) was added
  7. additionThe mixture was diluted in ether (15 mL)
  8. customtriturated for 15 minutes
  9. filtrationthe solids were filtered
  10. washwashed with ether and hexanes
  11. customdried

Sources & evidence

ORD record
ord-da2d955af21d49c997c53609584928ed
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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