Hydrochloric Acid → HCID 69676525, compound

HRID 919572Notes

Reaction equation

HRID 919572 reaction equation
[S:1]([N:11]1[C:15]2[N:16]=[CH:17][N:18]=[C:19]([NH:20][C@@H:21]3[CH2:26][CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22]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>CO.O>[NH:23]1[CH2:24][CH2:25][CH2:26][C@@H:21]([NH:20][C:19]2[C:14]3[CH:13]=[CH:12][N:11]([S:1]([C:4]4[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=4)(=[O:3])=[O:2])[C:15]=3[N:16]=[CH:17][N:18]=2)[CH2:22]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69676524HCID 69676524, compound

Product 1

HCID 69676525HCID 69676525, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of (R)-tert-butyl 3-(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)piperidine-1-carboxylate (20 g, 42.5 mmol) in MeOH (100 mL) was added conc. HCl (100 mL) at 0° C. and the reaction mixture was stirred for 1.5 h. The solvent was removed in vacuo to give a residue which was dissolved in water (50 mL). The aqueous phase was washed with ether and the aqueous phase was adjusted to a pH 10. The aqueous layer was then extracted with EtOAc (3×30 mL), combined, dried (Na2SO4) and concentrated in vacuo to give the titled compound (15 g, 95%). 1H NMR (400 MHz, CDCl3): δ 8.41 (s, 1H), 8.03 (d, J=8.8 Hz, 2H), 7.42 (d, J=3.6 Hz, 1H), 7.28 (d, J=m 8.8 Hz, 2H), 6.77 (d, J=3.6 Hz, 1H), 6.43 (bs, 1H), 4.51 (bs, 1H), 3.18-3.09 (m, 3H), 2.95-2.84 (m, 2H), 2.37 (s, 3H), 1.95-1.88 (m, 2H), 1.81-1.78 (m, 1H), 1.66-1.63 (m, 1H). LCMS [M+1]: 372.

Workup

  1. customThe solvent was removed in vacuo
  2. customto give a residue which
  3. washThe aqueous phase was washed with ether
  4. extractionThe aqueous layer was then extracted with EtOAc (3×30 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1f41531a3f5149258b1d3addda86c4fd
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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