Triethylamine → 5'-(Cyclohexanecarbonyl-amino)-2'-chloro-biphenyl-4-carboxylic acid [4-(1,1-dioxo-1lambda*6*-thiomorpholin-4-ylmethyl)-phenyl]-amide

HRID 1678489Notes

Reaction equation

HRID 1678489 reaction equation
[CH:1]1([C:7]([NH:9][C:10]2[CH:11]=[CH:12][C:13]([Cl:25])=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([C:22](O)=[O:23])=[CH:18][CH:17]=3)[CH:15]=2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[O:26]=[S:27]1(=[O:41])[CH2:32][CH2:31][N:30]([CH2:33][C:34]2[CH:39]=[CH:38][C:37]([NH2:40])=[CH:36][CH:35]=2)[CH2:29][CH2:28]1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[O:41]=[S:27]1(=[O:26])[CH2:28][CH2:29][N:30]([CH2:33][C:34]2[CH:39]=[CH:38][C:37]([NH:40][C:22]([C:19]3[CH:20]=[CH:21][C:16]([C:14]4[CH:15]=[C:10]([NH:9][C:7]([CH:1]5[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]5)=[O:8])[CH:11]=[CH:12][C:13]=4[Cl:25])=[CH:17][CH:18]=3)=[O:23])=[CH:36][CH:35]=2)[CH2:31][CH2:32]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27796824-(4-Aminobenzyl)thiomorpholine 1,1-dioxideHCID 598223462'-Chloro-5'-(cyclohexanecarbonyl-amino)-biphenyl-4-carboxylic acid

Product 1

HCID 162219195'-(Cyclohexanecarbonyl-amino)-2'-chloro-biphenyl-4-carboxylic acid [4-(1,1-dioxo-1lambda*6*-thiomorpholin-4-ylmethyl)-phenyl]-amideYield 21.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5′-(cyclohexanecarbonyl-amino)-2′-chloro-biphenyl-4-carboxylic acid (100 mg), 4-(1,1-dioxo-1lambda*6*-thiomorpholin-4-ylmethyl)-phenylamine (67 mg), triethylamine (0.098 ml) and HBTU (159 mg) in dry DMF (5 ml) was stirred at 20 C for 18 h. The mixture was then evaporated to dryness and purified via reversed-phase preparative HPLC (eluting with acetonitrile/water) to afford the title compound as an orange solid (35 mg).

Workup

  1. customThe mixture was then evaporated to dryness
  2. custompurified via reversed-phase preparative HPLC (eluting with acetonitrile/water)

Sources & evidence

ORD record
ord-fe85b380ae40464dae7b8b8ae93b224f
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

Loading…