Hydrochloric Acid → HCID 89650393, compound

HRID 2409065Notes

Reaction equation

HRID 2409065 reaction equation
[Cl:1][C:2]1[C:6]2=[N:7][C:8]([C@@H:11]([NH:13][S@@](C(C)(C)C)=O)[CH3:12])=[CH:9][CH:10]=[C:5]2[NH:4][CH:3]=1.Cl>CO.O1CCOCC1>[Cl:1][C:2]1[C:6]2=[N:7][C:8]([C@@H:11]([NH2:13])[CH3:12])=[CH:9][CH:10]=[C:5]2[NH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86689870HCID 86689870, compound

Product 1

HCID 89650393HCID 89650393, compoundYield 137.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

To (R)—N—((S)-1-(3-chloro-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)-2-methylpropane-2-sulfinamide (1.08 g, 3.23 mmol) in anhydrous MeOH (10 mL) was added HCl (4.0 mol/L) in dioxane (14 mL). The reaction mixture was stirred at 40° C. under N2 for 16 h. Volatile solvent was removed under reduced pressure. The crude product was triturated with DCM until solid is seen. Light yellow solid was filtered and dried under a high vacuum to afford 868.2 mg (89.3%) of (5)-1-(3-chloro-1H-pyrrolo-[3,2-b]pyridin-5-yl)ethanamine as HCl salt. 1H NMR (400 MHz, DMSO) δ 11.90 (br s, 1H), 8.47 (br s, 3H), 7.93 (d, J=8.5 Hz, 1H), 7.90 (d, J=2.9 Hz, 1H), 7.37 (d, J=8.5 Hz, 1H), 4.60 (dt, J=12.4, 6.1 Hz, 1H), 1.56 (d, J=6.8 Hz, 3H); MS (ESI) m/z: 196 [M+1]+.

Workup

  1. customVolatile solvent was removed under reduced pressure
  2. customThe crude product was triturated with DCM until solid
  3. filtrationLight yellow solid was filtered
  4. customdried under a high vacuum

Sources & evidence

ORD record
ord-e5959e7760f54ea38531dacc780578a3
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

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