Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → 5-(cis-2,3,4a,5,6,10b-Hexahydro-1H-benzo[f]quinoline-4-carbonyl)-3,3-dimethyl-1,3-dihydro-indol-2-one

HRID 455427Notes

Reaction equation

HRID 455427 reaction equation
[CH3:1][C:2]1([CH3:15])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([OH:13])=O)[CH:9]=2)[NH:4][C:3]1=[O:14].[CH2:16]1[C@H:25]2[C@H:20]([CH2:21][CH2:22][C:23]3[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=32)[NH:19][CH2:18][CH2:17]1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>>[CH2:16]1[C@H:25]2[C@H:20]([CH2:21][CH2:22][C:23]3[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=32)[N:19]([C:11]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[NH:4][C:3](=[O:14])[C:2]3([CH3:1])[CH3:15])=[O:13])[CH2:18][CH2:17]1

Participants

4

Reactant 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12327022(4aS,10bR)-1,2,3,4,4a,5,6,10b-Octahydrobenzo[f]quinolineHCID 150778053,3-dimethyl-2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid

Product 1

HCID 866541295-(cis-2,3,4a,5,6,10b-Hexahydro-1H-benzo[f]quinoline-4-carbonyl)-3,3-dimethyl-1,3-dihydro-indol-2-oneYield 19%

Procedure

The title compound is prepared from 3,3-dimethyl-2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid and cis-1,2,3,4,4a,5,6,10b-octahydro-benzo[f]quinoline following a procedure analogous to that described in Example 1 [2-(7-aza-1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate is used]. Yield: 19% of theory; LC (method 4): tR=1.95 min; Mass spectrum (ESI+): m/z=375 [M+H]+.

Sources & evidence

ORD record
ord-197b56fc275c4321af3aa74e8aa948ff
Source dataset
uspto-grants-2013_07
Patent number
US08497281B2

Reaction notes

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