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Ammonia → 4-(5-(6-(4-Methylpyridin-2-ylamino)pyridin-2-yl)thiazol-2-yl)benzamide

HRID 1854627
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HRID 1854627 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[S:19][C:18]([C:20]4[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=4)=[N:17][CH:16]=3)[CH:12]=[CH:11][CH:10]=2)[CH:3]=1.N.[OH:29]O>CCO>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[S:19][C:18]([C:20]4[CH:27]=[CH:26][C:23]([C:24]([NH2:25])=[O:29])=[CH:22][CH:21]=4)=[N:17][CH:16]=3)[CH:12]=[CH:11][CH:10]=2)[CH:3]=1
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참가 물질

5

반응물 3

HCID 222Ammonia2회HCID 784Hydrogen Peroxide2회HCID 533122454-(5-(6-(4-Methylpyridin-2-ylamino)pyridin-2-yl)thiazol-2-yl)benzonitrile

생성물 1

HCID 533122444-(5-(6-(4-Methylpyridin-2-ylamino)pyridin-2-yl)thiazol-2-yl)benzamide

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
40 °C

실험 절차

4-(5-(6-(4-methylpyridin-2-ylamino)pyridin-2-yl)thiazol-2-yl)benzonitrile (Example 51, 40 mg, 0.11 mmol) was suspended in EtOH (8 ml). Aqueous ammonia (28-30%, 4 ml) was added followed by H2O2 (35%, 1 ml). The reaction mixture was stirred at 40° C. for 2.5 days. Aqueous ammonia (2 ml) and H2O2 (0.250 ml) were added and the reaction mixture was stirred a further 24 hours at 40° C. The reaction was partitioned between H2O (30 ml) and EtOAc (70 ml). After separation, the aqueous phase was extracted again with EtOAc (70 ml). After evaporation, and purification of the crude product by dry flash chromatography over SiO2 eluting with EtOAc/MeOH (5%-10%)/NEt3 (0.5%), 4-(5-(6-(4-methylpyridin-2-ylamino)pyridin-2-yl)thiazol-2-yl)benzamide was obtained as a yellow solid (46 mg, 74%). 1H NMR (300 MHz, DMSO-d6) δ 9.72 (br s, 1H), 8.59 (br s, 1H), 8.20-7.98 (m, 6H), 7.95 (d, J=8.6 Hz, 1H), 7.78-7.70 (m, 1H), 7.66 (d, J=8.8 Hz, 1H), 7.57-7.45 (m, 3H), 2.25 (s, 3H). (APCI+) m/z 388 (M+H)+.

후처리

  1. stirringthe reaction mixture was stirred a further 24 hours at 40° C
  2. customThe reaction was partitioned between H2O (30 ml) and EtOAc (70 ml)
  3. customAfter separation
  4. extractionthe aqueous phase was extracted again with EtOAc (70 ml)
  5. customAfter evaporation, and purification of the crude product
  6. dry with materialby dry flash chromatography over SiO2 eluting with EtOAc/MeOH (5%-10%)/NEt3 (0.5%)

출처 및 근거

ORD 기록
ord-2218a6f3b4994d40afa1942ead821c10
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08962665B2

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