Hydrochloric Acid → HCID 46214653, compound

HRID 2367181Notes

Reaction equation

HRID 2367181 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:16]=[C:15]3[C:11]([C:12]([NH:17]C(=O)C)=[N:13][NH:14]3)=[CH:10][CH:9]=2)[CH:5]=[C:4]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[N:3]=1.[ClH:27]>CO>[ClH:27].[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:16]=[C:15]3[C:11]([C:12]([NH2:17])=[N:13][NH:14]3)=[CH:10][CH:9]=2)[CH:5]=[C:4]([N:21]2[CH2:22][CH2:23][O:24][CH2:25][CH2:26]2)[N:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58504413HCID 58504413, compound

Product 2

HCID 313Hydrochloric AcidHCID 46214653HCID 46214653, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

In a 100 mL flask under argon was dissolved N-{6-[2-amino-6-(4-morpholinyl)-4-pyrimidinyl]-1H-indazol-3-yl}acetamide (0.15 g, 0.26 mmol) in CH3OH (10 mL). HCl (0.69 mL, 8.3 mmol, 12 M) was added and the reaction mixture was stirred at 60° C. for 4 hours. The mixture was cooled to room temperature and filtered. The solid was washed with hexanes to afford a HCl salt of the title compound (75 mg) as a light yellow solid. LC-MS (ES) m/z=312 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 3.73 (m, 4H), 3.89 (m, 4H), 6.98 (s, 1H), 7.66 (d, J=8.6 Hz, 1H), 8.08 (m, 2H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered
  3. washThe solid was washed with hexanes

Sources & evidence

ORD record
ord-b7f8a3059c77485eb7aacb33604e2187
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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