5-Amino-1-methyl-2-oxoindoline → N-Methyl-N-(3-{[2-(1-methyl-2-oxo-2,3-dihydro-1H-indol-5-ylamino)-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino]-methyl}-pyridin-2-yl)-methanesulfonamide

HRID 472420Notes

Reaction equation

HRID 472420 reaction equation
Cl[C:2]1[N:24]=[C:5]2[C:6]([NH:10][CH2:11][C:12]3[C:13]([N:18]([CH3:23])[S:19]([CH3:22])(=[O:21])=[O:20])=[N:14][CH:15]=[CH:16][CH:17]=3)=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[NH2:25][C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[N:31]([CH3:35])[C:30](=[O:36])[CH2:29]2.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[CH3:23][N:18]([C:13]1[C:12]([CH2:11][NH:10][C:6]2[C:5]3[N:4]([N:3]=[C:2]([NH:25][C:26]4[CH:27]=[C:28]5[C:32](=[CH:33][CH:34]=4)[N:31]([CH3:35])[C:30](=[O:36])[CH2:29]5)[N:24]=3)[CH:9]=[CH:8][CH:7]=2)=[CH:17][CH:16]=[CH:15][N:14]=1)[S:19]([CH3:22])(=[O:21])=[O:20]

Participants

4

Reactant 3

HCID 226924705-Amino-1-methyl-2-oxoindolineHCID 249469872,2'-Bis(dicyclohexylphosphino)-1,1'-biphenylHCID 67478948N-{3-[(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino)-methyl]-pyridin-2-yl}-N-methyl-methanesulfonamide

Product 1

HCID 59612447N-Methyl-N-(3-{[2-(1-methyl-2-oxo-2,3-dihydro-1H-indol-5-ylamino)-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino]-methyl}-pyridin-2-yl)-methanesulfonamide

Procedure

N-Methyl-N-(3-{[2-(1-methyl-2-oxo-2,3-dihydro-1H-indol-5-ylamino)-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino]-methyl}-pyridin-2-yl)-methanesulfonamide was prepared from N-{3-[(2-chloro-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino)-methyl]-pyridin-2-yl}-N-methyl-methanesulfonamide (75.0 mg, 0.204 mmol) and 5-amino-1-methyl-1,3-dihydro-indol-2-one (37.0 mg, 0.228 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (23.0 mg, 0.0421 mmol) as the ligand in a manner analogous to Example 2d. Product isolated as a green-brown foam (0.017 g, 17%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.41 (d, J=4.8 Hz, 1H), 7.85 (d, J=7.7 Hz, 1H), 7.81 (d, J=6.6 Hz, 1H), 7.65 (s, 1H), 7.38 (d, J=8.5 Hz, 1H), 7.30-7.25 (m, 1H), 6.78 (d, J=8.4 Hz, 1H), 6.66 (t, J=7.3 Hz, 1H), 6.62 (s, 1H), 6.31 (d, J=7.8 Hz, 1H), 5.31 (t, J=6.2 Hz, 1H), 4.76 (d, J=6.2 Hz, 2H), 3.57 (s, 2H), 3.32 (s, 3H), 3.21 (s, 3H), 3.09 (s, 3H). MS=493 (MH)+.

Sources & evidence

ORD record
ord-5efd491809d34639b31d8ca43eab5199
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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