Hydrochloric Acid → HCID 69676466, compound

HRID 919586Notes

Reaction equation

HRID 919586 reaction equation
[CH2:1]([N:4]([C:18]1[C:19]2[CH:26]=[CH:25][N:24]([S:27]([C:30]3[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=3)(=[O:29])=[O:28])[C:20]=2[N:21]=[CH:22][N:23]=1)[C@H:5]1[CH2:10][CH2:9][CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6]1)[CH2:2][CH3:3].Cl>O1CCOCC1>[NH:7]1[CH2:8][CH2:9][CH2:10][C@H:5]([N:4]([CH2:1][CH2:2][CH3:3])[C:18]2[C:19]3[CH:26]=[CH:25][N:24]([S:27]([C:30]4[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=4)(=[O:29])=[O:28])[C:20]=3[N:21]=[CH:22][N:23]=2)[CH2:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118906732HCID 118906732, compound

Product 1

HCID 69676466HCID 69676466, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of (S)-tert-butyl 3-(propyl(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate (300 mg, 0.58 mmol) in 1,4-dioxane (5 mL) was treated with 4 N HCl in 1,4-dioxane (10 mL) at rt for 1 h. The solvent was removed in vacuo and the residue was suspended in water (10 mL). The aqueous layer was adjusted to a pH 9 with solid NaHCO3 and the solution was extracted with EtOAc (3×25 mL). The combined organic layer was dried over Na2SO4, concentrated in vacuo to yield titled intermediate (241 mg, 83%), which was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6): δ 8.23 (1s, 1H), 7.98 (d, J=8.0 Hz, 2H), 7.69 and 7.65 (2d, 0.1=4.0 Hz, 1H), 7.43 (d, J=8.0 Hz, 2H), 6.81 (d, J=4.0 Hz, 1H), 3.69-3.64 (m, 3H), 3.51-3.47 (m, 2H), 3.25-3.18 (m, 2H), 52.85-2.83 (m, 1H), 2.35 (s, 3H), 1.94-1.89 (m, 2H), 1.79-1.76 (m, 1H), 1.55-1.53 (m, 1H), 1.16 and 0.93 (t, J=7.2 Hz, 3H). LC-MS: m/z [M+1]=414.

Workup

  1. customThe solvent was removed in vacuo
  2. extractionthe solution was extracted with EtOAc (3×25 mL)
  3. dry with materialThe combined organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3c661f13bc644e7ebb841b34c8e37658
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

Loading…