1,4-Dioxane hydrochloride → N-phenyl-2-amino-5-indan carboxamide hydrochloride

HRID 48430Notes

Reaction equation

HRID 48430 reaction equation
[C:1]1([NH:7][C:8]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[CH2:15][CH:14]([NH:19]C(OC(C)(C)C)=O)[CH2:13]3)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:27].O1CCOCC1>C(O)(=O)C>[ClH:27].[C:1]1([NH:7][C:8]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[CH2:15][CH:14]([NH2:19])[CH2:13]3)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 22719646N-phenyl-2-(tert-butoxycarbonylamino)-5-indan carboxamide

Product 1

HCID 22719628N-phenyl-2-amino-5-indan carboxamide hydrochloride

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Using N-phenyl-2-(tert-butoxycarbonylamino)-5-indan carboxamide (27 mg, 0.077 mmol), 4N hydrochloric acid-dioxane (2.0 ml) and acetic acid (6.0 ml), a similar procedure to Production Example 213 was carried out to obtain N-phenyl-2-amino-5-indan carboxamide hydrochloride. Then using ethanol (1 ml), triethylamine (0.50 ml, 3.6 mmol), 4-chloro-5-methylthieno[2,3-d]pyrimidine (18 mg, 1.0 mmol), a similar procedure to b) in Production Example 208 was carried out. The product obtained was purified by silica gel chromatography (hexane:ethyl acetate=4:1 to 1:1) to obtain the title compound (8 mg, 0.020 mmol) having the following physical properties:

Sources & evidence

ORD record
ord-3d42f364453c453c99d67f9fc8e73e1c
Source dataset
uspto-grants-2004_03
Patent number
US06703421B1

Reaction notes

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