Stannous chloride dihydrate → Fluoren-9-ylmethyl (3R)-3-(N-{(1R)-2-[4-(2-aminophenyl)piperazinyl]-1-[(4-chlorophenyl)methyl]-2-oxoethyl}carbamoyl)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

HRID 1242729Notes

Reaction equation

HRID 1242729 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:27][C:28]([C@H:30]2[CH2:39][C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH2:32][N:31]2[C:40]([O:42][CH2:43][CH:44]2[C:56]3[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=3[C:50]3[C:45]2=[CH:46][CH:47]=[CH:48][CH:49]=3)=[O:41])=[O:29])[C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N+:24]([O-])=O)[CH2:14][CH2:13]2)=[O:11])=[CH:4][CH:3]=1.O.O.Cl[Sn]Cl>>[NH2:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[N:15]1[CH2:14][CH2:13][N:12]([C:10](=[O:11])[C@H:9]([NH:27][C:28]([C@H:30]2[CH2:39][C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH2:32][N:31]2[C:40]([O:42][CH2:43][CH:44]2[C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][C:50]=3[C:51]3[C:56]2=[CH:55][CH:54]=[CH:53][CH:52]=3)=[O:41])=[O:29])[CH2:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:17][CH2:16]1

Participants

3

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 58714293Fluoren-9-ylmethyl (3r)-3-(n-{(1r)-1-[(4-chlorophenyl)methyl]-2-[4-(2-nitrophenyl)piperazinyl]-2-oxoethyl}carbamoyl)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

Product 1

HCID 58714327Fluoren-9-ylmethyl (3R)-3-(N-{(1R)-2-[4-(2-aminophenyl)piperazinyl]-1-[(4-chlorophenyl)methyl]-2-oxoethyl}carbamoyl)-1,2,3,4-tetrahydroisoquinoline-2-carboxylateYield 57.8%

Procedure

Fluoren-9-ylmethyl (3R)-3-(N-{(1R)-2-[4-(2-aminophenyl)piperazinyl]-1-[(4-chlorophenyl)methyl]-2-oxoethyl}carbamoyl)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate was prepared according to the procedure for Preparation II using fluoren-9-ylmethyl (3R)-3-(N-{(1R)-1-[(4-chlorophenyl)methyl]-2-[4-(2-nitrophenyl)-piperazinyl]-2-oxoethyl}carbamoyl)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate (1.4 g, 1.8 mmol) and SnCl2.2H2O (1.7 g, 7.3 mmol) (Aldrich). The crude product was purified by flash chromatography (SiO2, 1:1 EtOAc:hexane) and concentrated in vacuo to afford the desired compound (770 mg). MS (ESI, pos. ion) m/z: 740 (M+H), (ESI, neg. ion) m/z: 738 (M−H). Calc'd for C44H42ClN5O4: 739.29.

Workup

  1. customFluoren-9-ylmethyl (3R)-3-(N-{(1R)-2-[4-(2-aminophenyl)piperazinyl]-1-[(4-chlorophenyl)methyl]-2-oxoethyl}carbamoyl)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate was prepared
  2. customThe crude product was purified by flash chromatography (SiO2, 1:1 EtOAc:hexane)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4a967b681cf04a86bb345716253d6ffd
Source dataset
uspto-grants-2006_10
Patent number
US07115607B2

Reaction notes

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