Piperidine → HCID 57245952, compound

HRID 1737004Notes

Reaction equation

HRID 1737004 reaction equation
N1CCCCC1.[CH2:7]([C@@H:14]1[CH2:19][C@@H:18]([N:20]([CH2:27][C:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[N:31]=[CH:30][CH:29]=2)[C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])[CH2:17][CH2:16][N:15]1[C:38]([C@H:40]1[N:52](C(OCC2C3C=CC=CC=3C3C2=CC=CC=3)=O)[CH2:51][C:43]2[NH:44][C:45]3[C:50]([C:42]=2[CH2:41]1)=[CH:49][CH:48]=[CH:47][CH:46]=3)=[O:39])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CN(C)C=O>[CH2:7]([C@@H:14]1[CH2:19][C@@H:18]([N:20]([CH2:27][C:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[N:31]=[CH:30][CH:29]=2)[C:21](=[O:26])[C:22]([F:25])([F:23])[F:24])[CH2:17][CH2:16][N:15]1[C:38]([C@H:40]1[NH:52][CH2:51][C:43]2[NH:44][C:45]3[C:50]([C:42]=2[CH2:41]1)=[CH:49][CH:48]=[CH:47][CH:46]=3)=[O:39])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 57110034HCID 57110034, compound

Product 1

HCID 57245952HCID 57245952, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.97 ml, 19.9 mmol) of piperidine are added to a solution of 338 mg (0.399 mmol) of (2R*,4S*)-2-benzyl-1-((3S)-(2-(9-fluorenylmethyloxycarbonyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-3-yl)carbonyl)-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine in 3 ml of N,N-dimethylformamide, and the mixture is stirred at room temperature for 2 hours. It is then concentrated in a rotary evaporator, and the residue is chromatographed on silica gel with methylene chloride/methanol/conc. ammonia (2000:50:1) to separate the diastereomers. TLC: methylene chloride/methanol/conc. ammonia (700:50:1)

Workup

  1. concentrationIt is then concentrated in a rotary evaporator
  2. customthe residue is chromatographed on silica gel with methylene chloride/methanol/conc
  3. customammonia (2000:50:1) to separate the diastereomers

Sources & evidence

ORD record
ord-fa409bbd6df64979a720682fd399b5bc
Source dataset
uspto-grants-1996_07
Patent number
US05541195

Reaction notes

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