Hydrochloric Acid → HCID 86689832, compound

HRID 2409020Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[N:5][C:6]([C@@H:10]([NH:12][S@@](C(C)(C)C)=O)[CH3:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[ClH:19]>CO.O1CCOCC1>[ClH:19].[NH:1]1[C:9]2[C:4](=[N:5][C:6]([C@@H:10]([NH2:12])[CH3:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of (R)—N—((S)-1-(1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)-2-methylpropane-2-sulfinamide (597.0 mg, 2.25 mmol) in anhydrous MeOH (9 mL) was added HCl (4.0 mol/L) in dioxane (11 mL). The reaction mixture was stirred at 40° C. under N2 for 7 h. Volatile solvent was removed under reduced pressure. The crude product was triturated with MeOH/ether until solid is seen. The light yellow solid was filtered and dried under high vacuum to afford 524.0 mg (99.5%) of the desired product as HCl salt: 1H NMR (400 MHz, DMSO-d6) δ 12.57 (s, 1H), 9.00 (s, 3H), 8.42 (d, J=6.8 Hz, 1H), 8.10 (s, 1H), 7.74 (d, J=7.4 Hz, 1H), 6.79 (s, 1H), 4.88 (s, 1H), 1.67 (d, J=6.8 Hz, 3H); MS (ESI) m/z: 162.1 [M+1]+.

Workup

customVolatile solvent was removed under reduced pressure
customThe crude product was triturated with MeOH/ether until solid
filtrationThe light yellow solid was filtered
customdried under high vacuum

Sources & evidence

ORD record: ord-55de9d51448e414d943a056ad9c9ba00
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815877B2

Reaction notes

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