Hydrochloric Acid → 6-{4-[1-[2-(3-Chloro-propylamino)-ethyl]-4-(4-fluoro-3-methyl-phenyl)-1H-imidazol-2-yl]-piperidin-1-yl}-5-isopropyl-pyrimidin-4-ylamine

HRID 57146Notes

Reaction equation

HRID 57146 reaction equation
[N:1]1([CH2:5][CH2:6][N:7]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[C:14]([CH3:19])[CH:13]=3)[N:9]=[C:8]2[CH:20]2[CH2:25][CH2:24][N:23]([C:26]3[N:31]=[CH:30][N:29]=[C:28]([NH2:32])[C:27]=3[CH:33]([CH3:35])[CH3:34])[CH2:22][CH2:21]2)[CH2:4][CH2:3][CH2:2]1.[ClH:36].O1CCOCC1>CO>[Cl:36][CH2:4][CH2:3][CH2:2][NH:1][CH2:5][CH2:6][N:7]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[C:14]([CH3:19])[CH:13]=2)[N:9]=[C:8]1[CH:20]1[CH2:25][CH2:24][N:23]([C:26]2[N:31]=[CH:30][N:29]=[C:28]([NH2:32])[C:27]=2[CH:33]([CH3:35])[CH3:34])[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 118290344HCID 118290344, compound

Product 1

HCID 1182903246-{4-[1-[2-(3-Chloro-propylamino)-ethyl]-4-(4-fluoro-3-methyl-phenyl)-1H-imidazol-2-yl]-piperidin-1-yl}-5-isopropyl-pyrimidin-4-ylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 6-{4-[1-(2-azetidin-1-yl-ethyl)-4-(4-fluoro-3-methyl-phenyl)-1H-imidazol-2-yl]-piperidin-1-yl}-5-isopropyl-pyrimidin-4-ylamine (70.0 mg; 0.15 mmol; 1.0 eq.) in methanol (0.5 ml), was added 4.0M HCl in dioxane (0.37 ml; 1.47 mmol; 10.0 eq.). The reaction mixture was stirred at 40° C. for 72 hr. After removal of the solvents, the crude was purified by prep HPLC to afford the title compound. LC-MS (M+H=515, obsd=515).

Workup

  1. customAfter removal of the solvents
  2. customthe crude was purified by prep HPLC

Sources & evidence

ORD record
ord-5b35ac3814ac48d585e4d69f6b5907b6
Source dataset
uspto-grants-2016_09
Patent number
US09434714B2

Reaction notes

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