Triethylamine → (1R)-1-({4-[(2,3-Dihydro-1-benzofuran-5-ylmethyl)amino]-1-piperidinyl}methyl)-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dione hydrochloride

A suspension of (1R)-1-({4-[(1,2,3-benzothiadiazol-5-ylmethyl)amino]-1-piperidinyl}methyl)-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dione dihydrochloride (for a preparation see Example 5A(j)) (60 mg, 0.161 mmol) in chloroform (2 ml) and methanol (0.100 ml) at rt under nitrogen was treated with triethylamine (0.067 ml, 0.482 mmol) and stirred at rt for 15 min. The solution was then treated with 2,3-dihydro-1-benzofuran-5-carbaldehyde (commercially available) (0.020 ml, 0.161 mmol) and stirred for a further 30 min. The solution was then treated with sodium triacetoxyborohydride (102 mg, 0.482 mmol) and stirred at rt for 45 min. This was then treated with saturated aqueous NaHCO3 (10 ml) and extracted with 20% methanol/DCM (3×25 ml). The combined organic fractions were dried (NaSO4), filtered, evaporated and chromatographed (5-25% methanol/DCM) to give the free base of the title compound (24 mg, 34.5%) as a white solid.

1. stirringstirred for a further 30 min
2. stirringstirred at rt for 45 min
3. extractionextracted with 20% methanol/DCM (3×25 ml)
4. dry with materialThe combined organic fractions were dried (NaSO4)
5. filtrationfiltered
6. customevaporated
7. customchromatographed (5-25% methanol/DCM)

ORD record

ord-d9c9c45464a34d12b0e0c07b3428aa23

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08389524B2