2-Oxo-1,2-dihydroquinoxaline-6-carboxylic acid → 6-(cis-2,3,4,4a,9,9a-Hexahydro-indeno[2,1-b]pyridine-1-carbonyl)-1H-quinoxalin-2-one

HRID 521160Notes

Reaction equation

HRID 521160 reaction equation
[O:1]=[C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]([OH:14])=O)[CH:8]=2)[NH:3]1.[NH:15]1[CH2:20][CH2:19][CH2:18][C@@H:17]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=3[CH2:27][C@H:16]12.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>>[N:15]1([C:12]([C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[NH:3][C:2](=[O:1])[CH:11]=[N:10]3)=[O:14])[CH2:20][CH2:19][CH2:18][C@@H:17]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=3[CH2:27][C@H:16]12

Participants

4

Reactant 3

HCID 47499622-Oxo-1,2-dihydroquinoxaline-6-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58123900cis-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridine

Product 1

HCID 672242396-(cis-2,3,4,4a,9,9a-Hexahydro-indeno[2,1-b]pyridine-1-carbonyl)-1H-quinoxalin-2-oneYield 45%

Procedure

The title compound is prepared from 2-oxo-1,2-dihydro-quinoxaline-6-carboxylic acid and cis-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridine 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: 45% of theory; LC (method 4): tR=1.89 min; Mass spectrum (ESI+): m/z=346 [M+H]+.

Sources & evidence

ORD record
ord-0b6e75dbdf1946feae2d8e58050b8225
Source dataset
uspto-grants-2016_05
Patent number
US09328072B2

Reaction notes

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