(S)-ethyl 6-(4-((6-oxo-6,6a,7,8,9,10-hexahydro-5H-dipyrido[1,2-a:3',2'-e]pyrazin-3-yl)methyl)piperazin-1-yl)nicotinate → (S)-6-(4-((6-oxo-6,6a,7,8,9,10-hexahydro-5H-dipyrido[1,2-a:3',2'-e]pyrazin-3-yl)methyl)piperazin-1-yl)nicotinic acid

HRID 69636Notes

Reaction equation

HRID 69636 reaction equation
O=C1NC2C=C(CN3CCN(C4C=CC(C(O)=O)=CC=4)CC3)C=NC=2N2CCCC[C@@H]12.[O:32]=[C:33]1[NH:38][C:37]2[CH:39]=[C:40]([CH2:43][N:44]3[CH2:49][CH2:48][N:47]([C:50]4[CH:60]=[CH:59][C:53]([C:54]([O:56]CC)=[O:55])=[CH:52][N:51]=4)[CH2:46][CH2:45]3)[CH:41]=[N:42][C:36]=2[N:35]2[CH2:61][CH2:62][CH2:63][CH2:64][C@@H:34]12>>[O:32]=[C:33]1[NH:38][C:37]2[CH:39]=[C:40]([CH2:43][N:44]3[CH2:45][CH2:46][N:47]([C:50]4[CH:60]=[CH:59][C:53]([C:54]([OH:56])=[O:55])=[CH:52][N:51]=4)[CH2:48][CH2:49]3)[CH:41]=[N:42][C:36]=2[N:35]2[CH2:61][CH2:62][CH2:63][CH2:64][C@@H:34]12

Participants

3

Reactant 2

HCID 58324418(S)-ethyl 6-(4-((6-oxo-6,6a,7,8,9,10-hexahydro-5H-dipyrido[1,2-a:3',2'-e]pyrazin-3-yl)methyl)piperazin-1-yl)nicotinateHCID 58324508(S)-4-(4-((6-oxo-6,6a,7,8,9,10-hexahydro-5H-dipyrido [1,2-a:3',2'-e]pyrazin-3-yl)methyl)piperazin-1-yl)benzoic acid

Product 1

HCID 58324392(S)-6-(4-((6-oxo-6,6a,7,8,9,10-hexahydro-5H-dipyrido[1,2-a:3',2'-e]pyrazin-3-yl)methyl)piperazin-1-yl)nicotinic acid

Procedure

Compound 76B was prepared using a procedure analogous to that described in connection with Compound 73B except that (S)-ethyl 6-(4-((6-oxo-6,6a,7,8,9,10-hexahydro-5H-dipyrido[1,2-a:3′,2′-e]pyrazin-3-yl)methyl)piperazin-1-yl)nicotinate was used instead of (S)-ethyl 4-(4-((6-oxo-6,6a,7,8,9,10-hexahydro-5H-dipyrido[1,2-a:3′,2′-e]pyrazin-3-yl)methyl)piperazin-1-yl)benzoate to yield the title compound as a white solid. [M+H] calc'd for C22H26N6O3, 423; found, 423.

Workup

  1. customCompound 76B was prepared

Sources & evidence

ORD record
ord-40357e7e1f5841a6ad851ab6f8806669
Source dataset
uspto-grants-2014_09
Patent number
US08822470B2

Reaction notes

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