Acetic Acid → HCID 57028147, compound

HRID 1736989Notes

Reaction equation

HRID 1736989 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 retool) of sodium acetate, 134 μl (2.34 mmol) of acetic acid and 294 mg (1.87 mmol) 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-117aff9262e146e7ab6d1357d6e4bc22
Source dataset
uspto-grants-1996_07
Patent number
US05541195

Reaction notes

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