Hydrochloric Acid → 3-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-3-(piperidin-4-yl)propanenitrile

HRID 1852981Notes

Reaction equation

HRID 1852981 reaction equation
[C:1]([CH2:3][CH:4]([CH:25]1[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]1)[N:5]1[CH:9]=[C:8]([C:10]2[N:15]3[CH:16]=[CH:17][N:18]=[C:14]3[CH:13]=[C:12]([C:19]3[CH:20]=[N:21][N:22]([CH3:24])[CH:23]=3)[N:11]=2)[CH:7]=[N:6]1)#[N:2].C(Cl)[Cl:39].Cl.O1CCOCC1>>[ClH:39].[CH3:24][N:22]1[CH:23]=[C:19]([C:12]2[N:11]=[C:10]([C:8]3[CH:7]=[N:6][N:5]([CH:4]([CH:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)[CH2:3][C:1]#[N:2])[CH:9]=3)[N:15]3[CH:16]=[CH:17][N:18]=[C:14]3[CH:13]=2)[CH:20]=[N:21]1.[CH3:24][N:22]1[CH:23]=[C:19]([C:12]2[N:11]=[C:10]([C:8]3[CH:7]=[N:6][N:5]([CH:4]([CH:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)[CH2:3][C:1]#[N:2])[CH:9]=3)[N:15]3[CH:16]=[CH:17][N:18]=[C:14]3[CH:13]=2)[CH:20]=[N:21]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 312751,4-DioxaneHCID 86685306tert-butyl 4-(2-cyano-1-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)ethyl)piperidine-1-carboxylate

Product 2

HCID 866853073-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-3-(piperidin-4-yl)propanenitrile hydrochlorideHCID 866853083-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-3-(piperidin-4-yl)propanenitrileYield 236.4%

Procedure

Tert-butyl 4-(2-cyano-1-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)ethyl)piperidine-1-carboxylate (59.4 mg, 0.118 mmol) was dissolved in DCM (592 μL, 0.118 mmol). To this was added 4N HCl in dioxane (296 μL, 1.18 mmol) and stirred at ambient temperature for 1 hour. Complete conversion was observed after 1 hour and the reaction mixture was concentrated to dryness to afford the HCl salt of 3-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-3-(piperidin-4-yl)propanenitrile (56.0 mg, 99.7% yield). MS (apci) m/z=402.3 (M+H).

Workup

  1. waitComplete conversion was observed after 1 hour
  2. concentrationthe reaction mixture was concentrated to dryness

Sources & evidence

ORD record
ord-09a3f615c8234a4a8ba681533e67242a
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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