2-[4-(4-Aminophenyl)piperidin-1-yl]acetamide → HCID 137329043, compound

HRID 1262222Notes

Reaction equation

HRID 1262222 reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:25])([CH3:24])[C:8]1[CH:9]=[C:10]([C:14]2[N:22]3[C:17]([CH:18]=[N:19][C:20](O)=[N:21]3)=[CH:16][CH:15]=2)[CH:11]=[CH:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:26][C:27]1[CH:32]=[CH:31][C:30]([CH:33]2[CH2:38][CH2:37][N:36]([CH2:39][C:40]([NH2:42])=[O:41])[CH2:35][CH2:34]2)=[CH:29][CH:28]=1>>[C:1]([SiH2:5][O:6][C:7]([CH3:25])([CH3:24])[C:8]1[CH:9]=[C:10]([C:14]2[N:22]3[C:17]([CH:18]=[N:19][C:20]([NH:26][C:27]4[CH:32]=[CH:31][C:30]([CH:33]5[CH2:34][CH2:35][N:36]([CH2:39][C:40]([NH2:42])=[O:41])[CH2:37][CH2:38]5)=[CH:29][CH:28]=4)=[N:21]3)=[CH:16][CH:15]=2)[CH:11]=[CH:12][CH:13]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

3

Reactant 2

HCID 574161072-[4-(4-Aminophenyl)piperidin-1-yl]acetamideHCID 178455422HCID 178455422, compound

Product 1

HCID 137329043HCID 137329043, compound

Procedure

2-[4-(4-{7-[3-(tert-Butyl-dimethyl-silanyloxymethyl)-phenyl]-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino}-phenyl)-piperidin-1-yl]-acetamide was prepared from 7-[3-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-pyrrolo[2,1-f][1,2,4]triazin-2-ol and 2-[4-(4-Amino-phenyl)-piperidin-1-yl]-acetamide in an analogous manner to Example 1052a. Product isolated as an orange solid (104 mg, 54%). m.p.=170-173° C.; LCMS (m/e) 571 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 8.70 (s, 1H), 8.07 (s, 1H), 8.03 (d, 1H, J=7.8 Hz), 7.61 (d, 2H, J=8.3 Hz), 7.52-7.44 (m, 1H), 7.40 (d, 1H, J=7.5 Hz), 7.19 (d, 2H, J=8.3 Hz), 7.19-7.08 (m, 1H), 7.00 (d, 1H, J=4.7 Hz), 6.87-6.80 (m, 2H), 5.45 (bs, 1H), 4.88 (s, 2H), 3.05 (s, 2H), 3.06-2.97 (m, 2H), 2.58-2.43 (m, 1H), 2.38-2.25 (m, 2H), 1.94-1.85 (m, 2H), 1.85-1.70 (m, 2H), 0.97 (s, 9H), 0.13 (s, 6H).

Sources & evidence

ORD record
ord-3733971352da4fb9b5fce502b147d067
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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