Hydrochloric Acid → 4-piperazin-1-yl-3-[3-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrrol-1-yl]butanenitrile hydrochloride Salt

HRID 1772791Notes

Reaction equation

HRID 1772791 reaction equation
[C:1]([CH2:3][CH:4]([N:19]1[CH:23]=[CH:22][C:21]([C:24]2[C:25]3[CH:32]=[CH:31][N:30]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])[C:26]=3[N:27]=[CH:28][N:29]=2)=[CH:20]1)[CH2:5][N:6]1[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]1)#[N:2].[ClH:41]>O1CCOCC1>[ClH:41].[N:6]1([CH2:5][CH:4]([N:19]2[CH:23]=[CH:22][C:21]([C:24]3[C:25]4[CH:32]=[CH:31][N:30]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:38])([CH3:40])[CH3:39])[C:26]=4[N:27]=[CH:28][N:29]=3)=[CH:20]2)[CH2:3][C:1]#[N:2])[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67054978tert-butyl 4-{3-cyano-2-[3-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrrol-1-yl]propyl}piperazine-1-carboxylate

Product 1

HCID 670549144-piperazin-1-yl-3-[3-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrrol-1-yl]butanenitrile hydrochloride SaltYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of tert-butyl 4-{3-cyano-2-[3-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrrol-1-yl]propyl}piperazine-1-carboxylate (1.9 g, 0.0034 mol; peak 2 of Step 1) in 1,4-dioxane (20 mL) was added 4.0 M of HCl in p-dioxane (12 mL, 48 mmol). The mixture was stirred at room temperature for 80 minutes. Solvent was removed in vacua, to afford product as a light yellow solid (1.90 g, 100%). LCMS (M+H)+: 466.3.

Workup

  1. customSolvent was removed in vacua

Sources & evidence

ORD record
ord-7a5e32ec74474f4fa8da1826a9cfe7eb
Source dataset
uspto-grants-2016_02
Patent number
US09249145B2

Reaction notes

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