2,2'-Bis(dicyclohexylphosphino)-1,1'-biphenyl → N-{4-[2-({4-[(1,1-dioxidothiomorpholin-4-yl)methyl]phenyl}amino)[1,2,4]triazolo[1,5-a]pyridin-8-yl]phenyl}-N-methylmethanesulfonamide

HRID 472384Notes

Reaction equation

HRID 472384 reaction equation
[NH2:1][C:2]1[N:22]=[C:5]2[C:6]([C:10]3[CH:15]=[CH:14][C:13]([N:16]([CH3:21])[S:17]([CH3:20])(=[O:19])=[O:18])=[CH:12][CH:11]=3)=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.Br[C:24]1[CH:38]=[CH:37][C:27]([CH2:28][N:29]2[CH2:34][CH2:33][S:32](=[O:36])(=[O:35])[CH2:31][CH2:30]2)=[CH:26][CH:25]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[O:36]=[S:32]1(=[O:35])[CH2:33][CH2:34][N:29]([CH2:28][C:27]2[CH:37]=[CH:38][C:24]([NH:1][C:2]3[N:22]=[C:5]4[C:6]([C:10]5[CH:11]=[CH:12][C:13]([N:16]([CH3:21])[S:17]([CH3:20])(=[O:19])=[O:18])=[CH:14][CH:15]=5)=[CH:7][CH:8]=[CH:9][N:4]4[N:3]=3)=[CH:25][CH:26]=2)[CH2:30][CH2:31]1

Participants

4

Reactant 3

HCID 249469872,2'-Bis(dicyclohexylphosphino)-1,1'-biphenylHCID 523254684-(4-Bromo-benzyl)-thiomorpholine 1,1-dioxideHCID 67478821N-[4-(2-Amino-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-phenyl]-N-methyl-methanesulfonamide

Product 1

HCID 67481430N-{4-[2-({4-[(1,1-dioxidothiomorpholin-4-yl)methyl]phenyl}amino)[1,2,4]triazolo[1,5-a]pyridin-8-yl]phenyl}-N-methylmethanesulfonamide

Procedure

N-{4-[2-({4-[(1,1-dioxidothiomorpholin-4-yl)methyl]phenyl}amino)[1,2,4]triazolo[1,5-a]pyridin-8-yl]phenyl}-N-methylmethanesulfonamide was prepared from N-[4-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-phenyl]-N-methyl-methanesulfonamide (75.0 mg, 0.236 mmol) and 4-(4-bromo-benzyl)-thiomorpholine 1,1-dioxide (80.0 mg, 0.263 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 an orange solid (0.083 g, 65%). MP=177-180° C. 1H NMR (400 MHz, CDCl3, δ, ppm): 8.45 (dd, J=6.7, 1.1 Hz, 1H), 8.04 (d, J=8.6 Hz, 2H), 7.60-7.52 (m, 5H), 7.28 (d, J=8.5 Hz, 2H), 7.00 (t, J=6.9 Hz, 1H), 6.89 (s, 1H), 3.62 (s, 2H), 3.39 (s, 3H), 3.08-2.96 (m, 8H), 2.90 (s, 3H). MS=541 (MH)+.

Sources & evidence

ORD record
ord-33ae6390ddea448aa4347e7cd6a62e90
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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