Hydrochloric Acid → Hydrochloric Acid

HRID 2409556Notes

Reaction equation

HRID 2409556 reaction equation
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]

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×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

Product 2

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-d3f03a8596234c3e9ae7b45a0129e4a4
Source dataset
uspto-grants-2014_08
Patent number
US08815918B2

Reaction notes

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