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

HRID 1426173노트

반응식

HRID 1426173 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-da2d955af21d49c997c53609584928ed
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933077B2

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