2-(3-Isocyanatophenoxy)-6-methylpyrazine → N-{3-[(6-methylpyrazin-2-yl)oxy]phenyl}-3,6,8,9-tetrahydro-7H-pyrazolo[3,4-c][2,7]naphthyridine-7-carboxamide

HRID 2383460Notes

Reaction equation

HRID 2383460 reaction equation
FC(F)(F)C([O-])=O.[CH:8]1[C:20]2[C:19]3[CH2:18][CH2:17][NH2+:16][CH2:15][C:14]=3[CH:13]=[N:12][C:11]=2[NH:10][N:9]=1.[N:21]([C:24]1[CH:25]=[C:26]([CH:35]=[CH:36][CH:37]=1)[O:27][C:28]1[CH:33]=[N:32][CH:31]=[C:30]([CH3:34])[N:29]=1)=[C:22]=[O:23]>>[CH3:34][C:30]1[N:29]=[C:28]([O:27][C:26]2[CH:25]=[C:24]([NH:21][C:22]([N:16]3[CH2:15][C:14]4[CH:13]=[N:12][C:11]5[NH:10][N:9]=[CH:8][C:20]=5[C:19]=4[CH2:18][CH2:17]3)=[O:23])[CH:37]=[CH:36][CH:35]=2)[CH:33]=[N:32][CH:31]=1

Participants

3

Reactant 2

HCID 242296782-(3-Isocyanatophenoxy)-6-methylpyrazineHCID 866455766,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7-ium 2,2,2-trifluoroacetate

Product 1

HCID 59490528N-{3-[(6-methylpyrazin-2-yl)oxy]phenyl}-3,6,8,9-tetrahydro-7H-pyrazolo[3,4-c][2,7]naphthyridine-7-carboxamide

Procedure

The compound, N-{3-[(6-methylpyrazin-2-yl)oxy]phenyl}-3,6,8,9-tetrahydro-7H-pyrazolo[3,4-c][2,7]naphthyridine-7-carboxamide was prepared using 6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7-ium 2,2,2-trifluoroacetate and 2-(3-isocyanatophenoxy)-6-methylpyrazine as described in general procedure M. The product was obtained as a white solid; 400 MHz 1H NMR (DMSO-d6) δ: 13.59 (s, 1H), 8.86 (s, 2H), 8.34 (s, 1H), 8.3-8.25 (m, 2H), 8.17 (s, 1H), 7.4-7.26 (m, 3H), 6.8-6.74 (m, 1H), 4.77 (s, 2H), 3.82 (t, J=5.6 Hz, 2H), 3.14 (t, J=5.6 Hz, 2H), 2.35 (s, 3H); LCMS [M+H]: 402.

Workup

  1. customThe product was obtained as a white solid

Sources & evidence

ORD record
ord-3e609ed23e78424397792ff4669c6759
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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