Hydrochloric Acid → (S)-5-amino-N-(3-{[5-(4-methoxy-2-trifluoromethyl-phenylamino)-pyridin-2-ylmethyl]-carbamoyl}-tetrahydrofuran-3-yl)-nicotinamide

HRID 1428221Notes

Reaction equation

HRID 1428221 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][NH:17][C:18]([C@:20]3([NH:25][C:26]([C:28]4[CH:29]=[C:30]([NH:34]C(=O)OC(C)(C)C)[CH:31]=[N:32][CH:33]=4)=[O:27])[CH2:24][CH2:23][O:22][CH2:21]3)=[O:19])=[N:14][CH:15]=2)=[C:5]([C:42]([F:45])([F:44])[F:43])[CH:4]=1.Cl>O1CCOCC1>[NH2:34][C:30]1[CH:31]=[N:32][CH:33]=[C:28]([CH:29]=1)[C:26]([NH:25][C@@:20]1([C:18](=[O:19])[NH:17][CH2:16][C:13]2[CH:12]=[CH:11][C:10]([NH:9][C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=3[C:42]([F:44])([F:45])[F:43])=[CH:15][N:14]=2)[CH2:24][CH2:23][O:22][CH2:21]1)=[O:27]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68026201tert-Butyl(S)-[5-(3-{[5-(4-methoxy-2-trifluoromethyl-phenylamino)-pyridin-2-ylmethyl]-carbamoyl}-tetrahydrofuran-3-ylcarbamoyl)-pyridin-3-yl]-carbamate

Product 1

HCID 56840394(S)-5-amino-N-(3-{[5-(4-methoxy-2-trifluoromethyl-phenylamino)-pyridin-2-ylmethyl]-carbamoyl}-tetrahydrofuran-3-yl)-nicotinamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl(S)-[5-(3-{[5-(4-methoxy-2-trifluoromethyl-phenylamino)-pyridin-2-ylmethyl]-carbamoyl}-tetrahydrofuran-3-ylcarbamoyl)-pyridin-3-yl]-carbamate (product from Example 5e, 1.2 mmol) was stirred with a 4N HCl solution in dioxane (20 mL) for two hours at ambient temperature. Then the mixture was evaporated to dryness, the residue was triturated with approx. 20 mL diethyl ether and suction filtered.

Workup

  1. customThen the mixture was evaporated to dryness
  2. customthe residue was triturated with approx. 20 mL diethyl ether and suction
  3. filtrationfiltered

Sources & evidence

ORD record
ord-c99dd9d2a29e46d399066bab0246ed24
Source dataset
uspto-grants-2015_01
Patent number
US08937073B2

Reaction notes

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