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

HRID 1772765Notes

Reaction equation

HRID 1772765 reaction equation
[C:1]([CH2:3][CH:4]([N:19]1[CH:23]=[C:22]([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:21]=[N: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]=[C:22]([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:21]=[N:20]2)[CH2:3][C:1]#[N:2])[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 58180876tert-Butyl 4-{3-cyano-2-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propyl}piperazine-1-carboxylate

Product 1

HCID 670549114-piperazin-1-yl-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]butanenitrile hydrochloride

Procedure

tert-Butyl 4-{3-cyano-2-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propyl}piperazine-1-carboxylate (second peak from chiral purification, 0.70 g, 0.0012 mol) was stirred with 4.0 M of hydrogen chloride in p-dioxane (5.0 mL, 0.020 mol) at RT for 30 min. After evaporating to dryness, the resulting HCl salt was used directly in next step. LCMS calculated for C23H34N9OSi(M+H)+: m/z=467.3; Found: 467.0.

Workup

  1. customAfter evaporating to dryness

Sources & evidence

ORD record
ord-bb015540ef2c4c9aa0bc4c036e35866a
Source dataset
uspto-grants-2016_02
Patent number
US09249145B2

Reaction notes

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