5-Bromopyridine-2,3-diamine → HCID 59243060, compound

HRID 1644611Notes

Reaction equation

HRID 1644611 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([O:14][CH2:15][C:16]2[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][N:17]=2)[CH:13]=1)[CH:9]=O.[NH2:27][C:28]1[C:33]([NH2:34])=[CH:32][C:31]([Br:35])=[CH:30][N:29]=1>>[Br:35][C:31]1[CH:32]=[C:33]2[NH:34][C:9]([C:8]3[CH:11]=[C:12]([O:14][CH2:15][C:16]4[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][N:17]=4)[CH:13]=[C:6]([O:5][CH2:4][C:3]4[CH:23]=[CH:24][CH:25]=[CH:26][C:2]=4[F:1])[CH:7]=3)=[N:27][C:28]2=[N:29][CH:30]=1

Participants

3

Reactant 2

HCID 6911565-Bromopyridine-2,3-diamineHCID 59243031HCID 59243031, compound

Product 1

HCID 59243060HCID 59243060, compound

Procedure

The final product (217) was obtained using the procedure described for Example 191 except that 3-(2-fluorobenzyloxy)-5-((3-methylpyridin-2-yl)methoxy)benzaldehyde (217c) and 2,3-diamino-5-bromopyridine were used. 1H NMR (400 MHz, 90% DMSO-d6; 10% CDCl3) δ ppm 8.46 (br s, 1H), 8.39 (s, 1H), 8.11 (s, 1H), 7.78 (m, 1H), 7.52 (s, 1H), 7.48 (m, 1H), 7.45 (m, 2H), 7.40 (m, 2H), 7.16 (t, 1H, J=8.2 Hz), 7.08 (t, 1H, J=8.2 Hz), 6.79 (s, 1H), 5.32 (s, 2H), 5.19 (s, 2H), 2.31 (s, 3H). Calc'd for C26H20BrFN4O2; m/z (M+2H+)=521; found 521.

Sources & evidence

ORD record
ord-db61eb25dbf54cf58a46182764a79e6c
Source dataset
uspto-grants-2012_02
Patent number
US08124617B2

Reaction notes

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