Morpholine-4-carboximidamide Hydrobromide → HCID 178451771、化合物

HRID 1801553ノート

反応式

HRID 1801553 の反応式
Br.[N:2]1([C:8]([NH2:10])=[NH:9])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([C:24](=O)[CH2:25][C:26](OCC)=[O:27])[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].[N+](=C1CCCCCCCCCC1C1CCCCCCCCCC1)=[N-]>C(O)C>[C:11]([O:15][C:16]([N:18]1[CH2:19][CH2:20][CH:21]([C:24]2[CH:25]=[C:26]([OH:27])[N:10]=[C:8]([N:2]3[CH2:7][CH2:6][O:5][CH2:4][CH2:3]3)[N:9]=2)[CH2:22][CH2:23]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]

参加物

5

反応物 3

HCID 2806564Morpholine-4-carboximidamide HydrobromideHCID 6618868tert-Butyl 4-(3-ethoxy-3-oxopropanoyl)piperidine-1-carboxylateHCID 22171225HCID 22171225、化合物

生成物 1

HCID 178451771HCID 178451771、化合物収率 40.5%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Morpholine-4-carboxamidine hydrobromide (0.267 g) and 4-(2-ethoxycarbonylacetyl)-piperidine-1-carboxylic acid tert-butyl ester (0.38 g, 1.27 mmol) were stirred in ethanol (10 mL) and diazobicycloundecane (285 μl) was added. The reaction stirred for 18 hours at room temperature. The ethanol was removed under reduced pressure and water (25 mL) was added. The solution was acidified (to pH=4) with acetic acid. The product was extracted with dichloromethane (4×30 mL). The dichloromethane was removed and crude product was purified twice on silica gel (Combiflash), eluting with 10% methanol in dichloromethane to provide 4-(6-hydroxy-2-morpholin-4-ylpyrimidin-4-yl)-piperidine-1-carboxylic acid tert-butyl ester (0.15 g, 40.5% yield) as a white solid. 1H NMR (300 MHz, CDCl3/TMS): δ=5.63 (s, 1H), 4.25-4.05 (m, 2H), 3.75 (m, 8H), 2.75-2.65 (m, 2H), 2.47-2.35 (m, 1H), 1.00-1.75 (m, 2H), 1.70-1.50 (m, 2H), 1.46 (s, 9H). 13C NMR (75 MHz, CDCl3/TMS): δ=173.35, 166.87, 154.96, 154.06, 98.88, 79.70, 66.72, 45.13, 44.24, 30.64, 28.82, 27.58.

後処理

  1. customThe ethanol was removed under reduced pressure and water (25 mL)
  2. additionwas added
  3. extractionThe product was extracted with dichloromethane (4×30 mL)
  4. customThe dichloromethane was removed
  5. customcrude product was purified twice on silica gel (Combiflash)
  6. washeluting with 10% methanol in dichloromethane

出典と根拠

ORDレコード
ord-b3c6f987df6e4348ac105b018838cda3
出典データセット
uspto-grants-2013_01
特許番号
US08349833B2

反応ノート

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