Dichloromethane → 2-[4-(6-Methoxy-[1,5]naphthyridin-4-yl)phenyl]ethylamine hydrochloride salt

HRID 1435871Notes

Reaction equation

HRID 1435871 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[N:24]=3)[N:19]=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)(C)(C)C.FC(F)(F)C(O)=O.C(Cl)[Cl:37]>>[ClH:37].[CH3:27][O:26][C:23]1[N:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[N:19]=[CH:18][CH:17]=[C:16]2[C:13]1[CH:14]=[CH:15][C:10]([CH2:9][CH2:8][NH2:7])=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 57938632HCID 57938632, compound

Product 1

HCID 684436432-[4-(6-Methoxy-[1,5]naphthyridin-4-yl)phenyl]ethylamine hydrochloride salt

Procedure

To a stirred solution of {2-[4-(6-methoxy[1,5]naphthyridin-4-yl)phenyl]ethyl}carbamic acid tert-butyl ester (0.67 g, 1.76 mmole) in dry CH2Cl2 (75 mL) at RT was added trifluoroacetic acid (50 mL). After 2 h, the reaction solution was concentrated under vacuum and the residue dissolved in 4M HCl in dioxane (5 mL) at RT. After 1 hr, the reaction contents were concentrated and dried under high vacuum to give the crude title compound as a tan solid which was used immediately in the proceeding reaction: LC-MS (ES) m/e 280 (M+H)+.

Workup

  1. concentrationthe reaction solution was concentrated under vacuum
  2. dissolutionthe residue dissolved in 4M HCl in dioxane (5 mL) at RT
  3. waitAfter 1 hr
  4. customthe reaction contents
  5. concentrationwere concentrated
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-74623b3d8b9146a7a937b7a23ed8470e
Source dataset
uspto-grants-2009_11
Patent number
US07618959B2

Reaction notes

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