Hydrochloric Acid → HCID 178427344, compound

HRID 571715Notes

Reaction equation

HRID 571715 reaction equation
[S:1]([N:11]1[C:15]2[N:16]=[CH:17][N:18]=[C:19]([N:20]3[CH2:25][CH2:24][CH2:23][CH:22]([NH:26][C:27](=O)[O:28][C:29](C)([CH3:31])[CH3:30])[CH2:21]3)[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].Cl>O1CCOCC1>[C:15]([N:16]=[C:27]([O:28][C:29]1[CH:31]=[CH:10][CH:4]=[CH:5][CH:30]=1)[NH:26][CH:22]1[CH2:23][CH2:24][CH2:25][N:20]([C:19]2[C:14]3[CH:13]=[CH:12][N:11]([S:1]([C:4]4[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=4)(=[O:2])=[O:3])[C:15]=3[N:16]=[CH:17][N:18]=2)[CH2:21]1)#[N:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67969632HCID 67969632, compound

Product 1

HCID 178427344HCID 178427344, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution tert-butyl 1-(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-3-ylcarbamate (6.3 g, 20 mmol) in dioxane (50 ml) was added 4.0 N HCl (50 mL, 200 mmol) and stirred at rt. After several hours, the reaction mixture was concentrated in vacuo to give the deprotected amine. A solution of 1-(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-3-amine (580 mg, 1.29 mmol) and diphenyl cyanocarbonimidate (370 mg, 1.5 mmol) in DMF (20 mL) was heated at 65 C for 16 h. the reaction mixture was cooled to rt and diluted with EtOAc and water (1:2, 200 mL). The organic phase was separated washed subsequently with sat. NaHCO3 brine, water, dried (Na2SO4) and concentrated in vacuo to afford 155.

Workup

  1. waitAfter several hours
  2. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-4b11421474fd42589a0a5fa3a98ff2c7
Source dataset
uspto-grants-2015_05
Patent number
US09029359B2

Reaction notes

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