Hydrochloric Acid → Hydrochloric Acid

HRID 2409556ノート

反応式

HRID 2409556 の反応式
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:19]=[CH:18][C:17]([C:20]3[N:27]4[C:23]([S:24][C:25]([C:28]5[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([O:36][CH3:37])[CH:29]=5)=[N:26]4)=[N:22][CH:21]=3)=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:38]>O1CCOCC1>[CH3:37][O:36][C:30]1[CH:29]=[C:28]([C:25]2[S:24][C:23]3=[N:22][CH:21]=[C:20]([C:17]4[CH:18]=[N:19][C:14]([N:11]5[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]5)=[N:15][CH:16]=4)[N:27]3[N:26]=2)[CH:33]=[CH:32][C:31]=1[O:34][CH3:35].[ClH:38]

参加物

5

反応物 2

HCID 313Hydrochloric Acid2 回HCID 667169444-{5-[2-(3,4-Dimethoxy-phenyl)-imidazo[2,1-b][1,3,4]thiadiazol-5-yl]-pyrimidin-2-yl}-piperazine-1-carboxylic acid tert-butyl ester

生成物 2

HCID 313Hydrochloric Acid収率 77%HCID 667169502-(3,4-Dimethoxy-phenyl)-5-(2-piperazin-1-yl-pyrimidin-5-yl)-imidazo[2,1-b][1,3,4]thiadiazole

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒2 回

実験手順

To a suspension of 4-{5-[2-(3,4-Dimethoxy-phenyl)-imidazo[2,1-b][1,3,4]thiadiazol-5-yl]-pyrimidin-2-yl}-piperazine-1-carboxylic acid tert-butyl ester (0.105 g, 0.201 mmol, 1 eq) in dioxane (1.5 mL) was added 4M HCl in dioxane (0.5 mL, 0.2 mmol, 10 eq) at 0° C. The reaction was allowed to warm to it and it was stirred overnight. After 18 h additional HCl (0.5 mL) was added and the reaction was stirred for 7 h. Solvents were removed under reduced pressure and the residue was treated with CH3CN. Solids were filtered off and washed with CH3CN to give the desired product as HCl salt (72 mg, 77%). HPLC-MS: (5-40% B in 8 min, 0.8 mL/min, 50° C.): tR=4.68 min, [M+H]+ m/z 424.2; 1H NMR (300 MHz, DMSO) δ 8.97 (s, 2H), 7.69 (s, 1H), 7.56 (d, J=8.3 Hz, 1H), 7.49 (s, 1H), 7.16 (d, J=8.5 Hz, 1H), 3.89 (s, 3H), 3.86 (s, 3H), 3.75 (m, 4H), 2.79 (m, 4H).

後処理

  1. temperatureto warm to it and it
  2. stirringthe reaction was stirred for 7 h
  3. customSolvents were removed under reduced pressure
  4. additionthe residue was treated with CH3CN
  5. filtrationSolids were filtered off
  6. washwashed with CH3CN

出典と根拠

ORDレコード
ord-d3f03a8596234c3e9ae7b45a0129e4a4
出典データセット
uspto-grants-2014_08
特許番号
US08815918B2

反応ノート

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