Hydrochloric Acid → HCID 44600482, compound

HRID 1177608Notes

Reaction equation

HRID 1177608 reaction equation
Cl.O1CCOCC1.[F:8][C:9]1[CH:10]=[C:11]([C@@H:33]([NH:35][S@@](C(C)(C)C)=O)[CH3:34])[CH:12]=[CH:13][C:14]=1[C:15]1[S:16][C:17]2[C:22]([N:23]=1)=[CH:21][CH:20]=[C:19]([C:24]1([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:26][CH2:25]1)[N:18]=2>CO>[F:8][C:9]1[CH:10]=[C:11]([C@@H:33]([NH2:35])[CH3:34])[CH:12]=[CH:13][C:14]=1[C:15]1[S:16][C:17]2[C:22]([N:23]=1)=[CH:21][CH:20]=[C:19]([C:24]1([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:25][CH2:26]1)[N:18]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67111893HCID 67111893, compound

Product 1

HCID 44600482HCID 44600482, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydrogen chloride, 4.0 M solution in 1,4-dioxane (0.63 mL, 2.5 mmol) was added to a suspension of (R)-N-((S)-1-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)ethyl)-2-methylpropane-2-sulfinamide. (0.413 g, 0.84 mmol)) in methanol (60.00 mL). The yellow reaction mixture was allowed to stir at ambient temperature for 4 h. The crude reaction mixture was concentrated in vacuo and purified by silica gel chromatography to afford (S)-1-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)ethanamine. MS (ESI) m/z: calculated: 389.1; Observed: 390.1 (M++1).

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated in vacuo
  3. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-76ea565e336443c1b8040108154aed26
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

Loading…