4-Methylmorpholine → 2'-Chloro-5'-(3-cyclohexyl-ureido)-biphenyl-4-carboxylic acid {4-[4-(propane-1-sulfonyl)-piperazin-1-ylmethyl]-phenyl}-amide

HRID 1678521Notes

Reaction equation

HRID 1678521 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:10])=[CH:4][C:3]=1[C:18]1[CH:23]=[CH:22][C:21]([C:24](O)=[O:25])=[CH:20][CH:19]=1.[CH2:27]([S:30]([N:33]1[CH2:38][CH2:37][N:36]([CH2:39][C:40]2[CH:45]=[CH:44][C:43]([NH2:46])=[CH:42][CH:41]=2)[CH2:35][CH2:34]1)(=[O:32])=[O:31])[CH2:28][CH3:29].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C=O)C>[CH2:27]([S:30]([N:33]1[CH2:38][CH2:37][N:36]([CH2:39][C:40]2[CH:41]=[CH:42][C:43]([NH:46][C:24]([C:21]3[CH:22]=[CH:23][C:18]([C:3]4[CH:4]=[C:5]([NH:8][C:9]([NH:11][CH:12]5[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]5)=[O:10])[CH:6]=[CH:7][C:2]=4[Cl:1])=[CH:19][CH:20]=3)=[O:25])=[CH:44][CH:45]=2)[CH2:35][CH2:34]1)(=[O:31])=[O:32])[CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 282735484-[(4-(Propylsulfonyl)piperazin-1-yl)methyl]anilineHCID 673733282'-Chloro-5'-(3-cyclohexyl-ureido)-biphenyl-4-carboxylic acid

Product 1

HCID 673708212'-Chloro-5'-(3-cyclohexyl-ureido)-biphenyl-4-carboxylic acid {4-[4-(propane-1-sulfonyl)-piperazin-1-ylmethyl]-phenyl}-amideYield 14.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2′-Chloro-5′-(3-cyclohexyl-ureido)-biphenyl-4-carboxylic acid (150 mg), 4-(4-(propane-1-sulfonyl)-piperazin-1-ylmethyl)-phenylamine (236 mg) and HBTU (228 mg) in dry DMF (5 ml) containing N-methylmorpholine (0.13 ml) was stirred at room temp for 18 h. The mixture was then evaporated and the residue purified by chromatography. Gradient elution with 3%-20% 20DCM:8EtOH:1NH3 in DCM over 30 mins gave a white solid (38 mg)

Workup

  1. customThe mixture was then evaporated
  2. customthe residue purified by chromatography
  3. washGradient elution with 3%-20%

Sources & evidence

ORD record
ord-05497c3b64724012a4d16acb90c24e61
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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