Hydrochloric Acid → 2-(3-(4-(7-(1-isopropyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile hydrochloride

HRID 1853025Notes

Reaction equation

HRID 1853025 reaction equation
[C:1]([CH2:3][C:4]1([N:15]2[CH:19]=[C:18]([C:20]3[N:25]4[CH:26]=[CH:27][N:28]=[C:24]4[CH:23]=[C:22]([C:29]4[CH:30]=[N:31][N:32]([CH:34]([CH3:36])[CH3:35])[CH:33]=4)[N:21]=3)[CH:17]=[N:16]2)[CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5]1)#[N:2].[ClH:37].CO>O1CCOCC1>[ClH:37].[CH:34]([N:32]1[CH:33]=[C:29]([C:22]2[N:21]=[C:20]([C:18]3[CH:17]=[N:16][N:15]([C:4]4([CH2:3][C:1]#[N:2])[CH2:5][NH:6][CH2:7]4)[CH:19]=3)[N:25]3[CH:26]=[CH:27][N:28]=[C:24]3[CH:23]=2)[CH:30]=[N:31]1)([CH3:36])[CH3:35]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 67456728tert-butyl 3-(cyanomethyl)-3-(4-(7-(1-isopropyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)azetidine-1-carboxylate

Product 1

HCID 674569432-(3-(4-(7-(1-isopropyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile hydrochlorideYield 117.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a suspension of tert-butyl 3-(cyanomethyl)-3-(4-(7-(1-isopropyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)azetidine-1-carboxylate (0.090 g, 0.185 mmol) in 1.5 mL of dioxane was added hydrogen chloride (1.8 mL, 7.20 mmol) in dioxane at ambient temperature with stirring. After 2 hours, 0.5 mL of methanol was added to dissolve all solids and the reaction was concentrated under reduced pressure. The crude was suspended in DCM, sonicated, and concentrated three times and the resulting crude was dried on high vacuum for 3 hours to afford 2-(3-(4-(7-(1-isopropyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile hydrochloride (0.116 g, 0.217 mmol, 93% yield). MS (apci) m/z=388.2 (M+H).

Workup

  1. dissolutionto dissolve all solids
  2. concentrationthe reaction was concentrated under reduced pressure
  3. customsonicated
  4. concentrationconcentrated three times
  5. customthe resulting crude was dried on high vacuum for 3 hours

Sources & evidence

ORD record
ord-ae9b0caa399c4e58877f3ea9e3c170b5
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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