3-Aminoazetidine, 3-BOC protected → HCID 59548405, compound

HRID 1812136Notes

Reaction equation

HRID 1812136 reaction equation
COC1C=CC(C[N:8](CC2C=CC(OC)=CC=2)[C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]3[C:17]([NH:24][C:25]4[CH:26]=[N:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=4)=[N:18][CH:19]=[C:20]([CH:23]=3)[CH:21]=O)[N:10]=2)=CC=1.[NH:44]1[CH2:47][CH:46]([NH:48]C(=O)OC(C)(C)C)[CH2:45]1>>[NH2:48][CH:46]1[CH2:45][N:44]([CH2:21][C:20]2[CH:23]=[C:16]([C:11]3[N:12]=[C:13]([CH3:15])[N:14]=[C:9]([NH2:8])[N:10]=3)[C:17]([NH:24][C:25]3[CH:26]=[N:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=3)=[N:18][CH:19]=2)[CH2:47]1

Participants

3

Reactant 2

HCID 15194053-Aminoazetidine, 3-BOC protectedHCID 601552675-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)nicotinaldehyde

Product 1

HCID 59548405HCID 59548405, compound

Procedure

The title compound was synthesized following an analogous procedure to Example 220 using 5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)nicotinaldehyde (0.56 g, 0.969 mmol) and tert-butyl azetidin-3-ylcarbamate (Astatech, Bristol, Pa.) (0.250 g, 1.454 mmol). 1H NMR (400 MHz, d4-MeOH) δ 8.85 (d, 1H); 8.46 (d, J=2.54 Hz, 1H); 8.18 (d, J=2.35 Hz, 1H); 8.01 (dd, J=8.80, 2.74 Hz, 1H); 6.81 (d, J=8.80 Hz, 1H); 3.91 (s, 3H); 3.83-3.88 (m, 1H); 3.82 (s, 2H); 3.75 (t, J=7.92 Hz, 2H); 3.36-3.40 (m, 2H); 2.47 (s, 3H). m/z (ESI, +ve ion) 394.0 (M+H)+.

Sources & evidence

ORD record
ord-a2ae91c55b9b42ecbbd49ff25f19f66a
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

Loading…