Sodium Iodide → HCID 178430539、化合物

HRID 353107ノート

反応式

HRID 353107 の反応式
Cl.Cl[CH2:3][CH2:4][N:5]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.C(N(CC)CC)C.[CH3:19][CH:20]1[C:25]([CH3:37])([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]3[N:33]=[N:34][NH:35][CH:36]=3)[CH:27]=2)[CH2:24][CH2:23][NH:22][CH2:21]1.[I-].[Na+].C(=O)([O-])O.[Na+]>CN(C)C=O>[N:5]1([CH2:4][CH2:3][N:22]2[CH2:23][CH2:24][C:25]([CH3:37])([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]4[N:33]=[N:34][NH:35][CH:36]=4)[CH:27]=3)[CH:20]([CH3:19])[CH2:21]2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

参加物

7

反応物 5

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 24188283N-(2-chloroethyl)perhydroazepine hydrochlorideHCID 178430465HCID 178430465、化合物

生成物 1

HCID 178430539HCID 178430539、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

A solution of 1-(2-chloroethyl)perhydroazepine hydrochloride (42 mg, 0.21 mmol) in N,N-dimethylformamide (1 mL) was treated with triethylamine (30 μL, 0.22 mmol) then transferred to a flask containing 3,4-dimethyl-4-(3-(1H-1,2,3-triazol-4-yl)phenyl)piperidine (Preparation 44, 45 mg, 0.176 mmol) in N,N-dimethylformamide (2 mL). Sodium iodide (32 mg, 0.21 mmol) and sodium hydrogencarbonate (18 mg, 0.21 mmol) were added and the resultant mixture was heated at 60° C. overnight. The solvent was then removed in vacuo and the residue was partitioned between saturated aqueous sodium hydrogencarbonate solution (5 mL) and dichloromethane (5 mL). The phases were separated and the aqueous layer was further extracted with dichloromethane (2×5 mL). The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by reversed phase preparative HPLC (condition 2) to give the acetate salt of the title compound. The free base was obtained by treating with dilute aqueous ammonia solution (2 mL) and extracting with ether (4×3 mL). Drying over Na2SO4, filtering and evaporation to dryness gave the title compound as a white solid (16 mg, 24%).

後処理

  1. customthen transferred to a flask
  2. customThe solvent was then removed in vacuo
  3. customthe residue was partitioned between saturated aqueous sodium hydrogencarbonate solution (5 mL) and dichloromethane (5 mL)
  4. customThe phases were separated
  5. extractionthe aqueous layer was further extracted with dichloromethane (2×5 mL)
  6. dry with materialThe combined extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by reversed phase preparative HPLC (condition 2)

出典と根拠

ORDレコード
ord-cc29c784563940db9156b9fe7ec24042
出典データセット
uspto-grants-2004_06
特許番号
US06750231B2

反応ノート

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