Ethyl isocyanate → 1-(2-(2-(3-(Benzyloxy)pyridin-2-ylamino)thiazol-4-yl)ethyl)-3-ethylurea

HRID 1426175노트

반응식

HRID 1426175 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.[N:24]([CH2:27][CH3:28])=[C:25]=[O:26]>CN(C=O)C>[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:25]([NH:24][CH2:27][CH3:28])=[O:26])[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

4

반응물 2

HCID 8022Ethyl isocyanateHCID 866397044-(2-aminoethyl)-N-(3-(benzyloxy)pyridin-2-yl)thiazol-2-amine

생성물 1

HCID 166616061-(2-(2-(3-(Benzyloxy)pyridin-2-ylamino)thiazol-4-yl)ethyl)-3-ethylurea수율 30.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Crude 4-(2-aminoethyl)-N-(3-(benzyloxy)pyridin-2-yl)thiazol-2-amine (Example 134, Step A; 0.25 g, 0.766 mmol) was dissolved in DMF (20 mL), and isocyanatoethane (0.109 g, 1.53 mmol) was added. 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 purified via MPLC (Biotage) eluting with ethyl acetate to afford the title compound (0.092 g, 30.2% yield) as a light yellow powder. 1H NMR (DMSO-d6) δ 0.97 (t, 3H), 2.67 (t, 2H), 2.98 (m, 2H), 3.29 (m, 2H), 5.26 (s, 2H), 5.82 (bt, 2H), 6.64 (s, 1H), 6.88 (m, 1H), 7.32-7.43 (m, 4H), 7.58 (d, 2H), 7.85 (d, 1H), 7.95 (s, 1H), 9.91 (s, 1H).

후처리

  1. custompartitioned between ethyl acetate and water
  2. washThe organic layer was washed with water and brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified via MPLC (Biotage)
  6. washeluting with ethyl acetate

출처 및 근거

ORD 기록
ord-a0260233e9be47c580fdd12c9e752166
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933077B2

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