Hydrochloric Acid → HCID 67458429, compound

HRID 1853056Notes

Reaction equation

HRID 1853056 reaction equation
[C:1]([CH2:3][C:4]1([N:15]2[CH:19]=[CH:18][C:17]([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]([CH3:34])[CH:33]=4)[N:21]=3)=[N:16]2)[CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5]1)#[N:2].C(Cl)[Cl:36].Cl.O1CCOCC1>>[ClH:36].[CH3:34][N:32]1[CH:33]=[C:29]([C:22]2[N:21]=[C:20]([C:17]3[CH:18]=[CH:19][N:15]([C:4]4([CH2:3][C:1]#[N:2])[CH2:7][NH:6][CH2:5]4)[N:16]=3)[N:25]3[CH:26]=[CH:27][N:28]=[C:24]3[CH:23]=2)[CH:30]=[N:31]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 312751,4-DioxaneHCID 68231007HCID 68231007, compound

Product 1

HCID 67458429HCID 67458429, compoundYield 58.6%

Procedure

Tert-butyl 3-(cyanomethyl)-3-(3-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)azetidine-1-carboxylate (Example 129; 28.3 mg, 0.0616 mmol) was dissolved in DCM (308 μL, 0.0616 mmol) and treated with 4N HCl in dioxane (308 μL, 1.23 mmol). The reaction mixture was stirred at ambient temperature for 1 hour, then concentrated in vacuo to afford 2-(3-(3-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile hydrochloride (14.3 mg, 53.7% yield) as a white solid. MS (apci) m/z=360.2 (M+H).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-da3902c528ec4b0284081abfaa04be7b
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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