Hydrochloric Acid → (S)-1-(1-Methyl-6-(tetrahydro-2H-pyran-4-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine

HRID 75305Notes

Reaction equation

HRID 75305 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[N:6][C:7]([C@@H:17]([NH:19]C(=O)OC(C)(C)C)[CH3:18])=[C:8]([CH:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[CH:9]=2)[CH:4]=[CH:3]1.[ClH:27]>O1CCOCC1>[ClH:27].[CH3:1][N:2]1[C:10]2[C:5](=[N:6][C:7]([C@@H:17]([NH2:19])[CH3:18])=[C:8]([CH:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[CH:9]=2)[CH:4]=[CH:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 86708003(S)-tert-Butyl (1-(1-methyl-6-(tetrahydro-2H-pyran-4-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)carbamate

Product 2

HCID 313Hydrochloric AcidHCID 86708004(S)-1-(1-Methyl-6-(tetrahydro-2H-pyran-4-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamineYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
23 °C

Procedure

To a solution of (S)-tert-butyl (1-(1-methyl-6-(tetrahydro-2H-pyran-4-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)carbamate (515 mg, 1.361 mmol) in dioxane (5 mL) was added 4.0 M HCl in 1,4-dioxane (3.40 mL, 13.6 mmol) at 23° C. The mixture was stirred for 30 minutes at 23° C. Additional 4.0 M HCl (3.40 mL, 13.6 mmol) was added at 23° C. and the mixture was stirred for 1.5 hours. The reaction mixture was concentrated via rotary evaporation, re-suspended in Et2O (5 mL), filtered, and rinsed with Et2O. The resulting solid was dried in vacuo to give an HCl salt of the title compound as a yellow solid (403 mg, 100%). ESI-MS m/z [M+H]+ calc'd for C15H21N3O, 260; found 260.

Workup

  1. stirringthe mixture was stirred for 1.5 hours
  2. concentrationThe reaction mixture was concentrated via rotary evaporation
  3. filtrationfiltered
  4. washrinsed with Et2O
  5. customThe resulting solid was dried in vacuo

Sources & evidence

ORD record
ord-b17ebc8b766b4dbaa407aece016ab29f
Source dataset
uspto-grants-2014_09
Patent number
US08835420B2

Reaction notes

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