2-methyl-2,3-dihydro-1H-isoindol-5-amine → [8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(2-methyl-2,3-dihydro-1H-isoindol-5-yl)-amine

HRID 472445Notes

Reaction equation

HRID 472445 reaction equation
Cl[C:2]1[N:20]=[C:5]2[C:6]([C:10]3[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=3)=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[CH3:21][N:22]1[CH2:30][C:29]2[C:24](=[CH:25][CH:26]=[C:27]([NH2:31])[CH:28]=2)[CH2:23]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[CH3:19][S:16]([C:13]1[CH:14]=[CH:15][C:10]([C:6]2[C:5]3[N:4]([N:3]=[C:2]([NH:31][C:27]4[CH:28]=[C:29]5[C:24](=[CH:25][CH:26]=4)[CH2:23][N:22]([CH3:21])[CH2:30]5)[N:20]=3)[CH:9]=[CH:8][CH:7]=2)=[CH:11][CH:12]=1)(=[O:18])=[O:17]

Participants

4

Reactant 3

HCID 219881602-methyl-2,3-dihydro-1H-isoindol-5-amineHCID 249469872,2'-Bis(dicyclohexylphosphino)-1,1'-biphenylHCID 674814372-Chloro-8-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine

Product 1

HCID 59612568[8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(2-methyl-2,3-dihydro-1H-isoindol-5-yl)-amine

Procedure

[8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(2-methyl-2,3-dihydro-1H-isoindol-5-yl)-amine was prepared from 2-chloro-8-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine (75.0 mg, 0.244 mmol) and 2-methyl-2,3-dihydro-1H-isoindol-5-ylamine (40.0 mg, 0.270 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 yellow foam (0.049 g, 48%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.50 (d, J=6.7 Hz, 1H), 8.23 (d, J=8.4 Hz, 2H), 8.08 (d, J=8.3 Hz, 2H), 7.65 (d, J=7.3 Hz, 1H), 7.51 (s, 1H), 7.32 (d, J=8.3 Hz, 1H), 7.15 (d, J=8.1 Hz, 1H), 7.02 (t, J=7.0 Hz, 1H), 6.98 (s, 1H), 3.94 (s, 2H), 3.88 (s, 2H), 3.09 (s, 3H), 2.61 (s, 3H). MS=420 (MH)+.

Sources & evidence

ORD record
ord-1c61e3e1ca5f47339b95492a83a91872
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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