Methanol → 1-(4-(4-(4-(2-Aminophenoxy)-5-chloropyrimidin-2-ylamino)-3-methoxy phenyl)piperazin-1-yl)ethanone

HRID 2284907노트

반응식

HRID 2284907 반응식
[Cl:1][C:2]1[C:3]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[N+:33]([O-])=O)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][N:18]([C:21](=[O:23])[CH3:22])[CH2:17][CH2:16]3)=[CH:11][C:10]=2[O:24][CH3:25])=[N:6][CH:7]=1.O.[Cl-].[NH4+].CO>O1CCOCC1.C(Cl)(Cl)Cl.[Zn]>[NH2:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[O:26][C:3]1[C:2]([Cl:1])=[CH:7][N:6]=[C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][N:18]([C:21](=[O:23])[CH3:22])[CH2:17][CH2:16]3)=[CH:11][C:10]=2[O:24][CH3:25])[N:4]=1

참가 물질

8

반응물 4

HCID 887MethanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 86729634HCID 86729634, 화합물

생성물 1

HCID 867296351-(4-(4-(4-(2-Aminophenoxy)-5-chloropyrimidin-2-ylamino)-3-methoxy phenyl)piperazin-1-yl)ethanone

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 6212Chloroform용매HCID 312751,4-Dioxane용매

실험 절차

To a stirred solution of 1-(4-(4-(5-chloro-4-(2-nitrophenoxy)pyrimidin-2-ylamino)-3-methoxyphenyl)piperazin-1-yl)ethanone (140 mg, 0.28 mmol) in 1,4-dioxane:water (10 mL:4 mL), Zinc dust (81 mg, 1.4 mmol) and ammonium chloride (74 mg, 1.4 mmol) were added, and the mixture was stirred at rt for 30 min. TLC showed completion of starting material (TLC system:5% methanol in chloroform (Rf): 0.3). The reaction mixture was filtered, concentrated, diluted with water (20 mL) and extracted with ethyl acetate (3×10 mL). The organic layer was separated, dried over sodium sulphate, and concentrated. Crude compound was washed with n-pentane to obtain 1-(4-(4-(4-(2-aminophenoxy)-5-chloropyrimidin-2-ylamino)-3-methoxy phenyl)piperazin-1-yl)ethanone as a pale yellow solid. (Yield: 90 mg, 68.7%). 1HNMR (DMSO-d6) δ 8.30 (s, 1H), 7.90 (s, 1H), 7.35 (d, 1H), 7.00 (m, 2H), 6.80 (d, 1H), 6.58 (m, 2H), 6.20 (br s, 1H), 4.90 (br s, 2H), 3.75 (s, 3H), 3.55 (m, 4H), 3.05 (m, 2H), 2.95 (m, 2H), 2.02 (s, 3H). Step-4. Preparation of N-(2-(2-(4-(4-acetylpiperazin-1-yl)-2-methoxyphenylamino)-5-chloro pyrimidin-4-yloxy)phenyl)acrylamide:

후처리

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. additiondiluted with water (20 mL)
  4. extractionextracted with ethyl acetate (3×10 mL)
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated
  8. washCrude compound was washed with n-pentane

출처 및 근거

ORD 기록
ord-6c53ac7757f14280b424accb92e39574
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09145387B2

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