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

HRID 1428221
Notes
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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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-Dioxane
Solvent

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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08937073B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes