Hydrochloric Acid → Hydrochloric Acid

HRID 2409556노트

반응식

HRID 2409556 반응식
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]

참가 물질

5

반응물 2

HCID 313Hydrochloric Acid2회HCID 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

생성물 2

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d3f03a8596234c3e9ae7b45a0129e4a4
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815918B2

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