Triethylamine → HCID 9809784, compound

HRID 1837385Notes

Reaction equation

HRID 1837385 reaction equation
[N:1]1([CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]3[C:15]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[N:16][C:17]4[C:22]([C:23]=3[C:24]([OH:26])=O)=[CH:21][CH:20]=[C:19]([O:27][CH3:28])[C:18]=4[Br:29])[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[C:67]1([C@@H:73]([NH2:76])[CH2:74][CH3:75])[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1>>[C:67]1([C@@H:73]([NH:76][C:24]([C:23]2[C:22]3[C:17](=[C:18]([Br:29])[C:19]([O:27][CH3:28])=[CH:20][CH:21]=3)[N:16]=[C:15]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:14]=2[CH2:13][N:10]2[CH2:11][CH2:12][CH:7]([N:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[CH2:8][CH2:9]2)=[O:26])[CH2:74][CH3:75])[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 6993773(1S)-1-phenylpropan-1-amineHCID 23497684HCID 23497684, compound

Product 1

HCID 9809784HCID 9809784, compoundYield 16.5%

Procedure

Prepared as described in Example 2 from 2 g (3.7 mmol) of 3-[1,4′]bipiperidinyl-1′-ylmethyl-8-bromo-7-methoxy-2-phenyl-quinoline-4-carboxylic acid (compound of Description 29), 1.55 ml (11.1 mmol) of triethylamine (TEA) 1.82 g (4.8 mmol) of O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluroniumhexa-fluorophosphate (HBTU) and 0.75 g (5.5 mmol) of (S)-1-phenyl-propylamine The crude material was purified by flash column chromatography on 230-400 mesh silica gel, utilising a mixture of EtOAc/MeOH 95:5 containing 0.05% NH4OH (28%) affording 0.4 g of title compound. After trituration with iPr2O, 0.3 g of the title compound were recovered as a pale yellow solid.

Workup

  1. customPrepared
  2. customwas purified by flash column chromatography on 230-400 mesh silica gel, utilising
  3. additiona mixture of EtOAc/MeOH 95:5 containing 0.05% NH4OH (28%)

Sources & evidence

ORD record
ord-06c85204dc614186ae1572ead575ed43
Source dataset
uspto-grants-2004_08
Patent number
US06780875B2

Reaction notes

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