Hydrochloric Acid → HCID 67055034, compound

HRID 1772829Notes

Reaction equation

HRID 1772829 reaction equation
[ClH:1].[Si]([O:9][CH2:10][CH:11]1[N:16]([CH2:17][CH:18]([N:22]2[CH:26]=[C:25]([C:27]3[C:28]4[CH:35]=[CH:34][N:33]([CH2:36][O:37][CH2:38][CH2:39][Si:40]([CH3:43])([CH3:42])[CH3:41])[C:29]=4[N:30]=[CH:31][N:32]=3)[CH:24]=[N:23]2)[CH2:19][C:20]#[N:21])[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12]1)(C(C)(C)C)(C)C>O1CCOCC1>[ClH:1].[OH:9][CH2:10][CH:11]1[CH2:12][NH:13][CH2:14][CH2:15][N:16]1[CH2:17][CH:18]([N:22]1[CH:26]=[C:25]([C:27]2[C:28]3[CH:35]=[CH:34][N:33]([CH2:36][O:37][CH2:38][CH2:39][Si:40]([CH3:41])([CH3:43])[CH3:42])[C:29]=3[N:30]=[CH:31][N:32]=2)[CH:24]=[N:23]1)[CH2:19][C:20]#[N:21]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58180924HCID 58180924, compound

Product 1

HCID 67055034HCID 67055034, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

4.0 M of hydrogen chloride in p-dioxane (1.6 mL, 6.4 mmol) was added to a solution of tert-butyl 3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-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 (0.32 g, 0.45 mmol, a mixture of diastereomers from Step 3) in 1,4-dioxane (2 mL). After stirring for 80 min, solvent was removed from the mixture in vacuo to afford the product as a light yellow solid, which was used without further purification (270 mg). LCMS (M+H)+: 497.2.

Workup

  1. customsolvent was removed from the mixture in vacuo

Sources & evidence

ORD record
ord-701507f4b19d4e0ca24c345b4a0fe6b7
Source dataset
uspto-grants-2016_02
Patent number
US09249145B2

Reaction notes

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