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

HRID 2284907ノート

反応式

HRID 2284907 の反応式
[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

参加物

8

反応物 4

HCID 887MethanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 86729634HCID 86729634、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 6212Chloroform溶媒HCID 312751,4-Dioxane溶媒

実験手順

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:

後処理

  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

出典と根拠

ORDレコード
ord-6c53ac7757f14280b424accb92e39574
出典データセット
uspto-grants-2015_09
特許番号
US09145387B2

反応ノート

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