2,3-Dihydro[1,4]oxathiino[2,3-c]pyridine-7-carbaldehyde → 1-({4-[([1,3]oxathiolo[5,4-c]pyridin-6-ylmethyl)amino]-1-piperidinyl}methyl)-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dione

HRID 1943250Notes

Reaction equation

HRID 1943250 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH:9]2[N:19]3[C:20]4[N:11]([C:12](=[O:22])[CH:13]=[CH:14][C:15]=4[CH:16]=[CH:17][C:18]3=[O:21])[CH2:10]2)[CH2:4][CH2:3]1.COC1N=C2C(CCC(=O)N2C[C@@H]2CO2)=CC=1.[S:40]1[C:49]2[CH:48]=[C:47]([CH:50]=O)[N:46]=[CH:45][C:44]=2[O:43][CH2:42]C1>>[S:40]1[C:49]2[CH:48]=[C:47]([CH2:50][NH:1][CH:2]3[CH2:3][CH2:4][N:5]([CH2:8][CH:9]4[N:19]5[C:20]6[N:11]([C:12](=[O:22])[CH:13]=[CH:14][C:15]=6[CH:16]=[CH:17][C:18]5=[O:21])[CH2:10]4)[CH2:6][CH2:7]3)[N:46]=[CH:45][C:44]=2[O:43][CH2:42]1

Participants

4

Reactant 3

HCID 574231152,3-Dihydro[1,4]oxathiino[2,3-c]pyridine-7-carbaldehydeHCID 580017221-[(4-Amino-1-piperidinyl)methyl]-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dioneHCID 580017637-(Methyloxy)-1-[(2R)-2-oxiranylmethyl]-3,4-dihydro-1,8-naphthyridin-2(1H)-one

Product 1

HCID 251008121-({4-[([1,3]oxathiolo[5,4-c]pyridin-6-ylmethyl)amino]-1-piperidinyl}methyl)-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dione

Procedure

The title compound was prepared from 1-[(4-amino-1-piperidinyl)methyl]-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dione (2:1 mixture of S:R prepared analogously to Example 11(a-d)) but using 7-(methyloxy)-1-[(2R)-2-oxiranylmethyl]-3,4-dihydro-1,8-naphthyridin-2(1H)-one (for a synthesis see example 5(f)) and 2,3-dihydro[1,4]oxathiino[2,3-c]pyridine-7-carbaldehyde (for a synthesis see WO2004058144, Example 60) according to the general method of Example 12.

Workup

  1. addition2:1 mixture of S

Sources & evidence

ORD record
ord-b0d016b33afd40f0a2cab3a70c54de1b
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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