Acetic Acid → HCID 57028147, compound

HRID 264633Notes

Reaction equation

HRID 264633 reaction equation
[CH2:1]([C@@H:8]1[CH2:13][C@@H:12]([N:14]([CH2:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=[CH:24][CH:23]=2)[C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])[CH2:11][CH2:10][NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([BH3-])#N.[Na+].C([O-])(=O)C.[Na+].C(O)(=O)C.[N:45]1[C:54]2[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=2)[C:48]([CH:55]=O)=[CH:47][CH:46]=1.N>C(Cl)Cl.CO>[CH2:1]([C@@H:8]1[CH2:13][C@@H:12]([N:14]([CH2:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=[CH:24][CH:23]=2)[C:15](=[O:20])[C:16]([F:18])([F:19])[F:17])[CH2:11][CH2:10][N:9]1[CH2:55][C:48]1[C:49]2[C:54](=[CH:53][CH:52]=[CH:51][CH:50]=2)[N:45]=[CH:46][CH:47]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 222AmmoniaHCID 780724-QuinolinecarboxaldehydeHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 57202094(2R*,4S*)-2-Benzyl-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine

Product 1

HCID 57028147HCID 57028147, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

200 mg (0.468 mmol) of (2R*,4S*)-2-benzyl-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine are reacted in analogy to Example 11 with 88 mg (1.4 mmol) of sodium cyanoborohydride, 115 mg (1.4 mmol) of sodium acetate, 134 μl (2.34 mmol) of acetic acid and 294 mg (1.87 mmol) of quinoline-4-carboxaldehyde to give the product. TLC: methylene chloride/methanol/conc. ammonia (700:50:1) Rf =0.33, FD-MS: M+ =568.

Workup

  1. customto give the product

Sources & evidence

ORD record
ord-280beb62055b419abd069f444096731f
Source dataset
uspto-grants-1997_07
Patent number
US05646144

Reaction notes

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