Hydrochloric Acid → HCID 57433644, compound

HRID 1783828Notes

Reaction equation

HRID 1783828 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[C:16]2[CH:21]=[CH:20][N:19]=[C:18]([NH:22][CH:23]4[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]4)[N:17]=2)[CH:13]=[CH:12][S:11]3)=[CH:4][C:3]=1[O:36][CH3:37].[ClH:38]>O1CCOCC1.CCOCC>[ClH:38].[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[C:16]2[CH:21]=[CH:20][N:19]=[C:18]([NH:22][CH:23]4[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]4)[N:17]=2)[CH:13]=[CH:12][S:11]3)=[CH:4][C:3]=1[O:36][CH3:37]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57590667HCID 57590667, compound

Product 1

HCID 57433644HCID 57433644, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent2×

Procedure

The tert-butyl 4-({4-[6-(4-fluoro-3-methoxyphenyl)imidazo[2,1-b][1,3]thiazol-5-yl]pyrimidin-2-yl}amino)piperidine-1-carboxylate (0.713 g, 1.36 mmol) was dissolved in 15 ml of dioxane and treated with 7.5 ml of anhydrous 4N HCl in dioxane at room temperature (RT). The reaction mixture was stirred at room temperature for two hours. The mixture was then diluted with 25 ml of ether and stirred until product separated as a solid. Solid product was filtered and washed with ether. The solid was dissolved in MeOH (20 ml) and concentrated to dryness twice. The product was dried at high vacuum to yield 0.652g of yellow solid (bis HCl salt) (96%). 400 MHz 1H NMR (DMSO-d6 at 60° C.) δ: 9.32 (br. s, 1H), 8.10 (d, J=4.7 Hz, 1H), 7.61 (d, J=4.3 Hz, 1H), 7.39 (dd, J=8.2, 2.0 Hz, 1H), 7.33 (dd, J=11.3, 8.2 Hz, 1H), 7.19 (ddd, J=8.2, 4.3, 2.0 Hz, 1H), 6.56 (d, J=6.7 Hz, 1H), 4.30-4.20 (m, 1H), 3.86 (s, 3H), 3.40-3.32 (m, 2H), 3.12-2.96 (m, 2H), 2.22-2.12 (m, 2H), 1.99-1.86(m, 2H). LCMS: 425 [M+H].

Workup

  1. stirringstirred until product
  2. customseparated as a solid
  3. filtrationSolid product was filtered
  4. washwashed with ether
  5. dissolutionThe solid was dissolved in MeOH (20 ml)
  6. concentrationconcentrated to dryness twice
  7. customThe product was dried at high vacuum

Sources & evidence

ORD record
ord-d24943ef497042baa68dee089eabafa4
Source dataset
uspto-grants-2009_03
Patent number
US07501430B2

Reaction notes

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