Acetyl chloride → HCID 16040367, 화합물

HRID 273517노트

반응식

HRID 273517 반응식
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][C:4]=1[C:10]1[CH:34]=[C:33]([CH3:35])[C:13]2[N:14]=[C:15]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)=[CH:21][CH:20]=3)[N:16]=[N:17][C:12]=2[CH:11]=1.CCN(CC)CC.[C:43](Cl)(=[O:45])[CH3:44]>C(Cl)Cl>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][C:43](=[O:45])[CH3:44])=[CH:5][C:4]=1[C:10]1[CH:34]=[C:33]([CH3:35])[C:13]2[N:14]=[C:15]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)=[CH:21][CH:20]=3)[N:16]=[N:17][C:12]=2[CH:11]=1

참가 물질

5

반응물 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 248235674-Chloro-3-(5-methyl-3-{4-[2-(pyrrolidin-1-yl)ethoxy]anilino}-1,2,4-benzotriazin-7-yl)phenol--hydrogen chloride (1/1)

생성물 1

HCID 16040367HCID 16040367, 화합물수율 80.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-chloro-3-{5-methyl-3-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylamino]-benzo[1,2,4]triazin-7-yl}-phenol hydrochloride (1.0 equiv., 0.978 mmol) in DCM (30 mL) was added neat Et3N (10 equiv., 4.89 mmol) under an argon rich atmosphere and stirred for 10 minutes. Neat Acetyl chloride (1.2 equiv., 1.17 mmol) was added dropwise via syringe to the reaction mixture and allowed to stir at room temperature for 24 h. The reaction was quenched using saturated NaHCO3; the organics were dried over Na2SO4 and then concentrated down under reduced pressure. The resulting crude solid was then brought up in DCM and purified by flash chromatography using a solvent system of 85:10:5 (v/v/v) DCM/MeOH/Et3N. The fractions were concentrated under reduced pressure and precipitated out using 1:5 (v/v) DCM/hexanes to afford an orange solid (409.1 mg, 75% yield). 1H NMR (DMSO-d6): δ 1.68 (m, 4H), 2.29 (s, 3H), 2.51 (m, 4H), 2.63 (s, 3H), 2.78 (t, J=5.94 Hz, 2H), 4.07 (t, J=5.99 Hz, 2H), 6.99 (dd, J=7.05 Hz, 12.55 Hz, 2H), 7.27 (dd, J=5.90 Hz, 8.75 Hz, 1H), 7.41 (d, J=2.80 Hz, 1H), 7.67 (d, J=8.75 Hz, 1H), 7.85 (m, 1H), 7.93 (d, J=9.05 Hz, 2H), 8.17 (m, 1H), 10.83 (s, 1H). Rf=0.29 MS (ES+) m/z 520, LC retention time 2.57 minutes.

후처리

  1. stirringto stir at room temperature for 24 h
  2. customThe reaction was quenched
  3. dry with materialthe organics were dried over Na2SO4
  4. concentrationconcentrated down under reduced pressure
  5. custompurified by flash chromatography
  6. concentrationThe fractions were concentrated under reduced pressure
  7. customprecipitated out

출처 및 근거

ORD 기록
ord-fd3ea97043ca4a5aa7d2b60cb9739d9d
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456176B2

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