2-oxo-2,3-dihydro-1H-1,3-benzodiazole-5-carboxylic acid → 5-(cis-2,3,4a,5,6,10b-Hexahydro-1H-benzo[f]quinoline-4-carbonyl)-1,3-dihydro-benzoimidazol-2-one

HRID 2272075Notes

Reaction equation

HRID 2272075 reaction equation
[O:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]([OH:13])=O)=[CH:10][C:4]=2[NH:3]1.[CH2:14]1[C@H:23]2[C@H:18]([CH2:19][CH2:20][C:21]3[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=32)[NH:17][CH2:16][CH2:15]1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>>[CH2:14]1[C@H:23]2[C@H:18]([CH2:19][CH2:20][C:21]3[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=32)[N:17]([C:11]([C:9]2[CH:8]=[CH:7][C:5]3[NH:6][C:2](=[O:1])[NH:3][C:4]=3[CH:10]=2)=[O:13])[CH2:16][CH2:15]1

Participants

4

Reactant 3

HCID 7807572-oxo-2,3-dihydro-1H-1,3-benzodiazole-5-carboxylic acidHCID 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]quinoline

Product 1

HCID 866541245-(cis-2,3,4a,5,6,10b-Hexahydro-1H-benzo[f]quinoline-4-carbonyl)-1,3-dihydro-benzoimidazol-2-oneYield 14%

Procedure

The title compound is prepared from 2-oxo-2,3-dihydro-1H-benzoimidazole-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: 14% of theory; LC (method 4): tR=1.89 min; Mass spectrum (ESI+): m/z=348 [M+H]+.

Sources & evidence

ORD record
ord-eac61e1a5f7c45c69e44142e51f69712
Source dataset
uspto-grants-2015_09
Patent number
US09120769B2

Reaction notes

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