Hydrochloric Acid → HCID 67456826, compound

HRID 1852983Notes

Reaction equation

HRID 1852983 reaction equation
[C:1]([CH2:3][C:4]1([N:17]2[CH:21]=[C:20]([C:22]3[N:27]4[CH:28]=[CH:29][N:30]=[C:26]4[CH:25]=[C:24]([C:31]4[CH:32]=[N:33][N:34]([CH3:36])[CH:35]=4)[N:23]=3)[CH:19]=[N:18]2)[CH2:9][CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6][CH2:5]1)#[N:2].C(Cl)[Cl:38].Cl.O1CCOCC1>>[ClH:38].[CH3:36][N:34]1[CH:35]=[C:31]([C:24]2[N:23]=[C:22]([C:20]3[CH:19]=[N:18][N:17]([C:4]4([CH2:3][C:1]#[N:2])[CH2:5][CH2:6][NH:7][CH2:8][CH2:9]4)[CH:21]=3)[N:27]3[CH:28]=[CH:29][N:30]=[C:26]3[CH:25]=2)[CH:32]=[N:33]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 312751,4-DioxaneHCID 53497461Tert-butyl 4-(cyanomethyl)-4-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Product 1

HCID 67456826HCID 67456826, compoundYield 107.8%

Procedure

Tert-butyl 4-(cyanomethyl)-4-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate (Example 21; 17 mg, 0.035 mmol) was dissolved in DCM (170 μL, 0.035 mmol) and treated with 4N HCl in dioxane (170 μL, 0.70 mmol). After 90 minutes, the reaction mixture was concentrated in vacuo to afford 2-(4-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)piperidin-4-yl)acetonitrile hydrochloride (16 mg, 98% yield). MS (apci) m/z=388.3 (M+H).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-fd748c0d59cf4fd09070ff1f22da56a0
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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