Hydrochloric Acid → 2-(6-Methoxy-[1,5]naphthyridin-4-yl)4,5,6,7-tetrahydro-2H-indazol-5-ylamine

HRID 1518006Notes

Reaction equation

HRID 1518006 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:16][CH2:15][C:14]2[C:10](=[CH:11][N:12]([C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH3:28])[N:25]=4)[N:20]=[CH:19][CH:18]=3)[N:13]=2)[CH2:9]1)(C)(C)C.Cl.O1CCOCC1>C(Cl)Cl.CO>[CH3:28][O:27][C:24]1[N:25]=[C:26]2[C:21](=[CH:22][CH:23]=1)[N:20]=[CH:19][CH:18]=[C:17]2[N:12]1[CH:11]=[C:10]2[C:14]([CH2:15][CH2:16][CH:8]([NH2:7])[CH2:9]2)=[N:13]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59560627[2-(6-methoxy-[1,5]naphthyridin-4-yl)-4,5,6,7-tetrahydro-2H-indazol-5-yl]carbamic acid tert-butyl ester

Product 1

HCID 595606482-(6-Methoxy-[1,5]naphthyridin-4-yl)4,5,6,7-tetrahydro-2H-indazol-5-ylamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of [2-(6-methoxy-[1,5]naphthyridin-4-yl)-4,5,6,7-tetrahydro-2H-indazol-5-yl]-carbamic acid tert-butyl ester (317 mg, 0.800 mmol) in CH2Cl2 (3.6 mL) was added 4 M HCl in dioxane (3.40 mL, 13.7 mmol), and the solution was stirred at RT for 3.5 h. The solution was concentrated to afford a crude solid, which was dissolved in CH3OH (10 mL). Anionic exchange resin (550 Å OH, 100 mg) was added and the mixture was stirred for 20 min. The mixture was filtered, and the resin was washed with CH3OH (30 mL). The filtrate was concentrated to afford 234 mg (99% crude) of the title compound as a brown oil. MS (ESI): exact mass calculated for C16H17N5O, 295.14; m/z found, 296.3 [M+H]+. 1H NMR (400 MHz, CDCl3): 9.08 (s, 1H), 8.76 (d, J=5.1, 1H), 8.26 (d, J=9.1, 1H), 8.15 (d, J=5.1, 1H), 7.18 (d, J=9.1, 1H), 4.10 (s, 3H), 3.29-3.27 (m, 1H), 3.01-2.96 (m, 2H), 2.87-2.80 (m, 1H), 2.48-2.39 (m, 1H), 2.11-2.05 (m, 1H), 1.82-1.64 (m, 3H).

Workup

  1. concentrationThe solution was concentrated
  2. customto afford a crude solid, which
  3. additionAnionic exchange resin (550 Å OH, 100 mg) was added
  4. stirringthe mixture was stirred for 20 min
  5. filtrationThe mixture was filtered
  6. washthe resin was washed with CH3OH (30 mL)
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-df2f89cde2fc47ae9bc9edc48f303dcf
Source dataset
uspto-grants-2012_07
Patent number
US08232391B2

Reaction notes

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