Ammonia → HCID 57267314, compound

HRID 264639Notes

Reaction equation

HRID 264639 reaction equation
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.[CH2:21]([C@@H:28]1[CH2:33][C@@H:32]([N:34]([CH2:41][C:42]2[C:51]3[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=3)[N:45]=[CH:44][CH:43]=2)[C:35](=[O:40])[C:36]([F:39])([F:38])[F:37])[CH2:31][CH2:30][NH:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.N>C(Cl)Cl.CO>[CH2:21]([C@@H:28]1[CH2:33][C@@H:32]([N:34]([CH2:41][C:42]2[C:51]3[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=3)[N:45]=[CH:44][CH:43]=2)[C:35](=[O:40])[C:36]([F:38])([F:39])[F:37])[CH2:31][CH2:30][N:29]1[C:8](=[O:10])[CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8333Diphenylacetic AcidHCID 24386Thionyl ChlorideHCID 57202094(2R*,4S*)-2-Benzyl-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine

Product 1

HCID 57267314HCID 57267314, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

248 mg (1.17 mmol) of diphenylacetic acid are reacted in analogy to Example 2j first with 128 μl (1.76 mmol) of thionyl chloride and subsequently with 200 mg (0.468 mmol) of (2R*,4S*)-2-benzyl-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine to give the product. TLC: methylene chloride/methanol/conc. ammonia (700:50:1) Rf =0.45, FD-MS: M+ =621.

Workup

  1. customto give the product

Sources & evidence

ORD record
ord-eecddc77f3234ffbb4486d667bc8f5da
Source dataset
uspto-grants-1997_07
Patent number
US05646144

Reaction notes

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