Pyridine → n-[(1r)-1-[(4-Chlorophenyl)methyl]-2-oxo-2-(4-{2-[(phenylsulfonyl)amino]phenyl}piperazinyl)ethyl]((3s)(3-1,2,3,4-tetrahydroisoquinolyl))carboxamide

HRID 1242757Notes

Reaction equation

HRID 1242757 reaction equation
CS(NC1C=CC=CC=1N1CCN(C(OC(C)(C)C)=O)CC1)(=O)=O.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][C@@H:33]([NH:58][C:59]([C@@H:61]2[CH2:70][C:69]3[C:64](=[CH:65][CH:66]=[CH:67][CH:68]=3)[CH2:63][N:62]2C(OC(C)(C)C)=O)=[O:60])[C:34](=[O:57])[N:35]2[CH2:40][CH2:39][N:38]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=3[NH:47][S:48]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)(=[O:50])=[O:49])[CH2:37][CH2:36]2)=[CH:28][CH:27]=1.NC1C=CC=CC=1N1CCN(C(=O)[C@H](NC([C@@H]2CC3C(=CC=CC=3)CN2C(OC(C)(C)C)=O)=O)CC2C=CC(Cl)=CC=2)CC1.N1C=CC=CC=1.C1(S(Cl)(=O)=O)C=CC=CC=1>>[Cl:25][C:26]1[CH:27]=[CH:28][C:29]([CH2:32][C@@H:33]([NH:58][C:59]([C@@H:61]2[CH2:70][C:69]3[C:64](=[CH:65][CH:66]=[CH:67][CH:68]=3)[CH2:63][NH:62]2)=[O:60])[C:34](=[O:57])[N:35]2[CH2:36][CH2:37][N:38]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=3[NH:47][S:48]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)(=[O:49])=[O:50])[CH2:39][CH2:40]2)=[CH:30][CH:31]=1

Participants

6

Reactant 5

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 21935212Tert-Butyl 4-(2-[(Methylsulfonyl)Amino]Phenyl)-PiperazinecarboxylateHCID 58714321tert-butyl 3-(N-{(1R)-2-[4-(2-aminophenyl)piperazinyl]-1-[(4-chlorophenyl)methyl]-2-oxoethyl}carbamoyl)(3S)-1,2,3,4-tetrahydroisoquinoline-2-carboxylateHCID 69077217Tert-butyl 3-{n-[(1r)-1-[(4-chlorophenyl)methyl]-2-oxo-2-(4-{2-[(phenylsulfonyl)-amino]phenyl}piperazinyl)ethyl]carbamoyl}(3s)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

Product 1

HCID 10168556n-[(1r)-1-[(4-Chlorophenyl)methyl]-2-oxo-2-(4-{2-[(phenylsulfonyl)amino]phenyl}piperazinyl)ethyl]((3s)(3-1,2,3,4-tetrahydroisoquinolyl))carboxamide

Procedure

Following the procedure for the synthesis of Preparation III, tert-butyl 3-{N-[(1R)-1-[(4-chlorophenyl)methyl]-2-oxo-2-(4-{2-[(phenylsulfonyl)-amino]phenyl}piperazinyl)ethyl]carbamoyl}(3S)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate was prepared from tert-butyl 3-(N-{(1R)-2-[4-(2-aminophenyl)piperazinyl]-1-[(4-chlorophenyl)methyl]-2-oxoethyl}carbamoyl)(3S)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate (Preparation IX) (771 mg, 1.247 mmol), pyridine (110 μl, 1.4 mmol) and benzenesulfonyl chloride (160 μl, 1.3 mmol) (Aldrich). The crude was purified by flash chromatography (SiO2, 10% EtOAc in CH2Cl2) to afford 330 mg of the desired compound. MS (ESI, pos. ion) m/z: 758 (M+H), (ESI, neg. ion) m/z: 756 (M−H). Calc'd for C40H44ClN5O6S: 758.33. Anal. Calcd for C40H44ClN5O6S-0.5 C4H8O2: C, 62.87; H, 6.03; N, 8.73; Cl, 4.42. Found C, 62.49; H, 6.03; N, 8.52.

Workup

  1. customThe crude was purified by flash chromatography (SiO2, 10% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-7417094fee1a4cc78699a9cc9a964d2b
Source dataset
uspto-grants-2006_10
Patent number
US07115607B2

Reaction notes

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