Triethylamine → HCID 57322859, compound

HRID 1737034Notes

Reaction equation

HRID 1737034 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.S(Cl)(Cl)=O.[CH2:15]([C@@H:22]1[CH2:27][C@@H:26]([N:28]([CH2:35][C:36]2[C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[N:39]=[CH:38][CH:37]=2)[C:29](=[O:34])[C:30]([F:33])([F:32])[F:31])[CH2:25][CH2:24][NH:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>>[CH2:15]([C@@H:22]1[CH2:27][C@@H:26]([N:28]([CH2:35][C:36]2[C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[N:39]=[CH:38][CH:37]=2)[C:29](=[O:34])[C:30]([F:32])([F:33])[F:31])[CH2:25][CH2:24][N:23]1[C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([Br:1])[CH:3]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 114563-Bromobenzoic acidHCID 24386Thionyl ChlorideHCID 57202094(2R*,4S*)-2-Benzyl-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine

Product 1

HCID 57322859HCID 57322859, compoundYield 95%

Procedure

141 mg (0.70 mmol) of m-bromobenzoic acid are reacted in analogy to Example 2a first with 2 ml (27 mmol) of thionyl chloride and subsequently with 200 mg (0.468 mmol) of (2R*,4S*)-2-benzyl-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine and 118 μl (0.842 mmol) of triethylamine to give the title compound (271 mg, 95%). TLC: methylene chloride/methanol/conc. ammonia (700:50:1) Rf =0.71, FD-MS: M+ =609, 611.

Sources & evidence

ORD record
ord-4f72f4f508fc47c883958c6abba38a0e
Source dataset
uspto-grants-1996_07
Patent number
US05541195

Reaction notes

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