N-[3-[6-[4-[(2R)-1,4-Dimethyl-3-oxopiperazin-2-yl]anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide → N-[3-(6-{4-[(2S)-1,4-Dimethyl-3-oxopiperazin-2-yl]anilino}-4-methyl-5-oxo-4,5-dihydropyrazin-2-yl)-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide

HRID 1363497Notes

Reaction equation

HRID 1363497 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH3:8])[C:4](=[O:9])[C@H:3]1[C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[C:18](=[O:43])[N:19]([CH3:42])[CH:20]=[C:21]([C:23]3[C:24]([CH3:41])=[C:25]([NH:29][C:30]([C:32]4[S:36][C:35]5[CH2:37][CH2:38][CH2:39][CH2:40][C:34]=5[CH:33]=4)=[O:31])[CH:26]=[CH:27][CH:28]=3)[N:22]=2)=[CH:12][CH:11]=1>C(Cl)(Cl)Cl>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH3:8])[C:4](=[O:9])[C@@H:3]1[C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:17]2[C:18](=[O:43])[N:19]([CH3:42])[CH:20]=[C:21]([C:23]3[C:24]([CH3:41])=[C:25]([NH:29][C:30]([C:32]4[S:36][C:35]5[CH2:37][CH2:38][CH2:39][CH2:40][C:34]=5[CH:33]=4)=[O:31])[CH:26]=[CH:27][CH:28]=3)[N:22]=2)=[CH:14][CH:15]=1

Participants

3

Reactant 1

HCID 25234918N-[3-[6-[4-[(2R)-1,4-Dimethyl-3-oxopiperazin-2-yl]anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide

Product 1

HCID 25234917N-[3-(6-{4-[(2S)-1,4-Dimethyl-3-oxopiperazin-2-yl]anilino}-4-methyl-5-oxo-4,5-dihydropyrazin-2-yl)-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The racemic mixture (12) was subjected to chiral separation on Chiralcel-AD-H (60% isopropanol in heptane, with 0.1% trifluoroacetic acid) to give individual enantiomers at 4.6 minutes (20) ((−) isomer) ([α]D25=−37.8° (c=3.75, CHCl3), mp=181-183° C.) and at 9.2 minutes (19) ((+) isomer) ([α]D25=+38.8° (c=3.57, CHCl3), mp=180-182° C.). Alternatively, the racemic mixture (12) was subjected to chiral separation on Chiralpak AD (75% isopropanol in heptane, at 1 mL/min) and individual enantiomers were collected from 17 to 27 minutes (20) ((−) isomer) and from 27 to 60 minutes (19) ((+) isomer).

Workup

  1. customThe racemic mixture (12) was subjected to chiral separation on Chiralcel-AD-H (60% isopropanol in heptane, with 0.1% trifluoroacetic acid)
  2. customto give individual enantiomers at 4.6 minutes (20) ((−) isomer) ([α]D25=−37.8° (c=3.75, CHCl3), mp=181-183° C.)
  3. customAlternatively, the racemic mixture (12) was subjected to chiral separation on Chiralpak AD (75% isopropanol in heptane, at 1 mL/min) and individual enantiomers
  4. customwere collected from 17 to 27 minutes (20) ((−) isomer) and from 27 to 60 minutes (19) ((+) isomer)

Sources & evidence

ORD record
ord-97f5aba886984055ac90c0b93e2e7aa5
Source dataset
uspto-grants-2011_02
Patent number
US07884108B2

Reaction notes

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