Pyridine → Tert-butyl 3-(n-((1r)-1-[(4-chlorophenyl)methyl]-2-oxo-2-[4-(2-{[(2,4,6-trimethylphenyl)sulfonyl]amino}phenyl) piperidyl]ethyl)carbamoyl)(3s)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

HRID 489699Notes

Reaction equation

HRID 489699 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:44])[C@H:15]([NH:24][C:25]([C@@H:27]2[CH2:36][C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH2:29][N:28]2[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[O:26])[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[CH2:10][CH2:9]1.[C:45]1([CH3:57])[CH:50]=[C:49]([CH3:51])[CH:48]=[C:47]([CH3:52])[C:46]=1[S:53](Cl)(=[O:55])=[O:54].N1C=CC=CC=1>ClCCCl>[Cl:23][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][C@@H:15]([NH:24][C:25]([C@@H:27]2[CH2:36][C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH2:29][N:28]2[C:37]([O:39][C:40]([CH3:41])([CH3:43])[CH3:42])=[O:38])=[O:26])[C:14](=[O:44])[N:11]2[CH2:12][CH2:13][CH:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[NH:1][S:53]([C:46]3[C:47]([CH3:52])=[CH:48][C:49]([CH3:51])=[CH:50][C:45]=3[CH3:57])(=[O:55])=[O:54])[CH2:9][CH2:10]2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 130462-Mesitylenesulfonyl chlorideHCID 10189232tert-Butyl 3-(N-{(1R)-2-[4-(2-aminophenyl)-piperidyl]-1-[(4-chlorophenyl)methyl]-2-oxoethyl}-carbamoyl)(3S)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

Product 1

HCID 23587444Tert-butyl 3-(n-((1r)-1-[(4-chlorophenyl)methyl]-2-oxo-2-[4-(2-{[(2,4,6-trimethylphenyl)sulfonyl]amino}phenyl) piperidyl]ethyl)carbamoyl)(3s)-1,2,3,4-tetrahydroisoquinoline-2-carboxylateYield 73.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The title compound was prepared according to the procedure described in Example 21 (Step a) by treating tert-butyl 3-(N-{(1R)-2-[4-(2-aminophenyl)piperidyl]-1-[(4-chlorophenyl)methyl]-2-oxoethyl}carbamoyl)(3S)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate (Example 20) (154 mg, 0.25 mmol) with 2-mesitylenesulfonyl chloride (Aldrich) (55 mg, 0.25 mmol) and pyridine (0.03 mL, 0.375 mmol) in 1,2-dichloroethane (10 mL). Purification by silica gel chromatography (100% EtOAc) provided the title compound as a white foam (146 mg). MS (ESI, pos. ion) m/z: 799 (M+1); MS (ESI, neg. ion) m/z: 797 (M−1) Calc'd for C44H51ClN4O6S: 798.32.

Workup

  1. customThe title compound was prepared
  2. customPurification by silica gel chromatography (100% EtOAc)

Sources & evidence

ORD record
ord-add5fee06aa04b239183cd033590904d
Source dataset
uspto-grants-2005_12
Patent number
US06977264B2

Reaction notes

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