tert-Butyl 4-(5-aminopyridin-2-yl)piperidine-1-carboxylate → (1',2',3',4',5',6'-Hexahydro-[2,4]bipyridinyl-5-yl)-[7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-amine

HRID 1262185Notes

Reaction equation

HRID 1262185 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1[N:37]2[C:32]([CH:33]=[N:34][C:35](O)=[N:36]2)=[CH:31][CH:30]=1>>[N:15]1[CH:16]=[C:17]([NH:20][C:35]2[N:34]=[CH:33][C:32]3=[CH:31][CH:30]=[C:29]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[O:22][CH3:21])[N:37]3[N:36]=2)[CH:18]=[CH:19][C:14]=1[CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

3

Reactant 2

HCID 59128562tert-Butyl 4-(5-aminopyridin-2-yl)piperidine-1-carboxylateHCID 1784892767-(2-Methoxyphenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ol

Product 1

HCID 46851866(1',2',3',4',5',6'-Hexahydro-[2,4]bipyridinyl-5-yl)-[7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-amine

Procedure

This example was prepared by using 5-Amino-3′,4′,5′,6′-tetrahydro-2′H-[2,4]bipyridinyl-1′-carboxylic acid tert-butyl ester (WO2006/047277) and 7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ol as described in Example 1255c followed by deprotection as described in Example 1223. 1H-NMR (DMSO) δ 9.7 (s, 1H), 9.0 (s, 1H), 8.8 (s, 1H), 8.6 (m, 1H), 8.3 (m, 1H), 8.1 (d, J=8.5 Hz, 1H), 7.7 (d, J=7.5 Hz, 1H), 7.5 (t, 1H), 7.2 (m, 2H), 7.1 (t, 1H), 7.0 (m, 2H), 3.8 (s, 3H), 3.4 (m, 2H), 3.0 (m, 3H), 2.0 (m, 2H), 1.85 (m, 2H); LC/MS (ESI+): 401 (M+H).

Sources & evidence

ORD record
ord-6c8e80a0213d4459883bcfcd35e5799b
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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