4-(1-Methylpiperidin-4-yl)aniline → HCID 59612594, compound

HRID 1889928Notes

Reaction equation

HRID 1889928 reaction equation
Cl[C:2]1[N:24]=[C:5]2[C:6]([NH:10][C:11]3[CH:23]=[CH:22][CH:21]=[CH:20][C:12]=3[CH2:13][N:14]([CH3:19])[S:15]([CH3:18])(=[O:17])=[O:16])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[CH3:25][N:26]1[CH2:31][CH2:30][CH:29]([C:32]2[CH:37]=[CH:36][C:35]([NH2:38])=[CH:34][CH:33]=2)[CH2:28][CH2:27]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[CH3:19][N:14]([CH2:13][C:12]1[CH:20]=[CH:21][CH:22]=[CH:23][C:11]=1[NH:10][C:6]1[C:5]2[N:4]([N:3]=[C:2]([NH:38][C:35]3[CH:36]=[CH:37][C:32]([CH:29]4[CH2:28][CH2:27][N:26]([CH3:25])[CH2:31][CH2:30]4)=[CH:33][CH:34]=3)[N:24]=2)[CH:9]=[CH:8][CH:7]=1)[S:15]([CH3:18])(=[O:17])=[O:16]

Participants

4

Reactant 3

HCID 219595294-(1-Methylpiperidin-4-yl)anilineHCID 249469872,2'-Bis(dicyclohexylphosphino)-1,1'-biphenylHCID 67479285HCID 67479285, compound

Product 1

HCID 59612594HCID 59612594, compound

Procedure

N-Methyl-N-(2-{2-[4-(1-methyl-piperidin-4-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino}-benzyl)-methanesulfonamide was prepared from N-[2-(2-chloro-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino)-benzyl]-N-methyl-methanesulfonamide (75.0 mg, 0.205 mmol) and 4-(1-methyl-piperidin-4-yl)-phenylamine (44.0 mg, 0.231 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (25.0 mg, 0.0457 mmol) as the ligand in a manner analogous to Example 2d. Product isolated as a tan foam (0.068 g, 64%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.96 (d, J=6.5 Hz, 1H), 7.54 (d, J=8.3 Hz, 2H), 7.46-7.38 (m, 2H), 7.35 (t, J=7.5 Hz, 1H), 7.21 (d, J=8.4 Hz, 2H), 7.13 (t, J=7.5 Hz, 1H), 7.00 (s, 1H), 6.83 (d, J=7.8 Hz, 1H), 6.76 (s, 1H), 6.70 (t, J=7.0 Hz, 1H), 4.36 (s, 2H), 2.95 (d, J=11.2 Hz, 2H), 2.91 (s, 3H), 2.78 (s, 3H), 2.50-2.40 (m, 1H), 2.33 (s, 3H), 2.10-2.00 (m, 2H), 1.87-1.73 (m, 4H). MS=520 (MH)+.

Sources & evidence

ORD record
ord-6bc23590ccb943d7922a7c115d80ab3c
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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