Hydrochloric Acid → HCID 86685319, compound

HRID 1853029Notes

Reaction equation

HRID 1853029 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([C:13]3([CH2:24][C:25]#[N:26])[CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]3)[CH:12]=2)[N:5]2[CH:27]=[CH:28][N:29]=[C:4]2[CH:3]=1.Cl>O1CCOCC1>[ClH:1].[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([C:13]3([CH2:24][C:25]#[N:26])[CH2:16][NH:15][CH2:14]3)[CH:12]=2)[N:5]2[CH:27]=[CH:28][N:29]=[C:4]2[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86685321HCID 86685321, compound

Product 1

HCID 86685319HCID 86685319, compoundYield 216.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a suspension of tert-butyl 3-(4-(7-chloroimidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-3-(cyanomethyl)azetidine-1-carboxylate (Preparation N; 0.050 g, 0.12 mmol) in 1 mL of dioxane was added hydrogen chloride (0.5 mL, 2.0 mmol) as a 4M solution in dioxane at ambient temperature. The reaction mixture was stirred for 2.5 hours. The solvent was then removed under a stream of nitrogen at ambient temperature overnight. About 5% of the starting material was observed, so the crude material was subjected to the reaction conditions outlined above for 1 hour and the solvent was again removed under a stream of nitrogen to afford 2-(3-(4-(7-chloroimidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile hydrochloride (0.059 g, 0.13 mmol, 106% yield). MS (apci) m/z=314.1 (M+H).

Workup

  1. customThe solvent was then removed under a stream of nitrogen at ambient temperature overnight
  2. customwas subjected to the reaction conditions
  3. customoutlined above for 1 hour
  4. customthe solvent was again removed under a stream of nitrogen

Sources & evidence

ORD record
ord-546e344eb46645e69a70ef6183a83a84
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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