(E)-3-{8-[2-(4-Ethyl-2-thienyl)ethyl]-2-morpholino-4-oxo-4H-pyrido[1,2-a]-pyrimidin-3-yl}-2-propenoic acid → tert-Butyl (E)-3-{8-({[4-(tert-butyl)-1,3-thiazol-2-yl]amino}carbonyl)-2-[(3S)-3-formyloxyhexahydro-1-pyridinyl]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoate

HRID 1828469Notes

Reaction equation

HRID 1828469 reaction equation
C(C1C=C(CCC2C=CN3C(=O)C(/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27])=C(N4CCOCC4)N=C3C=2)SC=1)C.[CH:32]([O:34][C@H:35]1[CH2:40][CH2:39][CH2:38][N:37]([C:41]2[N:42]=[C:43]3[CH:53]=[C:52]([C:54]([NH:56][C:57]4[S:58][CH:59]=[C:60]([C:62]([CH3:65])([CH3:64])[CH3:63])[N:61]=4)=[O:55])[CH:51]=[CH:50][N:44]3[C:45](=[O:49])[C:46]=2C=O)[CH2:36]1)=[O:33]>>[C:62]([C:60]1[N:61]=[C:57]([NH:56][C:54]([C:52]2[CH:51]=[CH:50][N:44]3[C:45](=[O:49])[C:46](/[CH:24]=[CH:25]/[C:26]([O:28][C:52]([CH3:54])([CH3:53])[CH3:51])=[O:27])=[C:41]([N:37]4[CH2:38][CH2:39][CH2:40][C@H:35]([O:34][CH:32]=[O:33])[CH2:36]4)[N:42]=[C:43]3[CH:53]=2)=[O:55])[S:58][CH:59]=1)([CH3:65])([CH3:64])[CH3:63]

Participants

3

Reactant 2

HCID 22063594(E)-3-{8-[2-(4-Ethyl-2-thienyl)ethyl]-2-morpholino-4-oxo-4H-pyrido[1,2-a]-pyrimidin-3-yl}-2-propenoic acidHCID 23581308(3S)-1-[8-({[4-(tert-butyl)-1,3-thiazol-2-yl]amino}carbonyl)-3-formyl-4-oxo-4H-pyrido-[1,2-a]pyrimidin-2-yl]hexahydro-3-pyridinyl formate

Product 1

HCID 86588110tert-Butyl (E)-3-{8-({[4-(tert-butyl)-1,3-thiazol-2-yl]amino}carbonyl)-2-[(3S)-3-formyloxyhexahydro-1-pyridinyl]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoateYield 100%

Procedure

Reactions were performed in the same manner as in Example 1, (J) by using (3S)-1-[8-({[4-(tert-butyl)-1,3-thiazol-2-yl]amino}carbonyl)-3-formyl-4-oxo-4H-pyrido-[1,2-a]pyrimidin-2-yl]hexahydro-3-pyridinyl formate (524 mg, 1.083 mmol), and the resulting residue was purified by silica gel column chromatography (chloroform→chloroform:methanol=100:1→70:1→50:1) to obtain 742 mg (100% or more) of the title compound as a brown oily substance in a mixture containing byproducts.

Workup

  1. customthe resulting residue was purified by silica gel column chromatography (chloroform→chloroform:methanol=100:1→70:1→50:1)

Sources & evidence

ORD record
ord-e628eca0e2b14f90a51644c064730b81
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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