tert-Butyl (E)-3-[8-{[(4-cyclobutyl-1,3-thiazol-2-yl)amino]carbonyl}-2-(3-formyloxy-piperidino)-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl]-2-propenoate → tert-Butyl (E)-3-[8-{[(4-cyclobutyl-1,3-thiazol-2-yl)amino]carbonyl}-2-(3-hydroxy-piperidino)-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl]-2-propenoate

HRID 1828459Notes

Reaction equation

HRID 1828459 reaction equation
OC1N=C2C=C(OCC3SC=C(C(C)C)N=3)C=CN2C(=O)C=1/C=C/C(OC(C)(C)C)=O.[CH:32]1([C:36]2[N:37]=[C:38]([NH:41][C:42]([C:44]3[CH:72]=[CH:71][N:47]4[C:48](=[O:70])[C:49](/[CH:61]=[CH:62]/[C:63]([O:65][C:66]([CH3:69])([CH3:68])[CH3:67])=[O:64])=[C:50]([N:52]5[CH2:57][CH2:56][CH2:55][CH:54]([O:58]C=O)[CH2:53]5)[N:51]=[C:46]4[CH:45]=3)=[O:43])[S:39][CH:40]=2)[CH2:35][CH2:34][CH2:33]1>>[CH:32]1([C:36]2[N:37]=[C:38]([NH:41][C:42]([C:44]3[CH:72]=[CH:71][N:47]4[C:48](=[O:70])[C:49](/[CH:61]=[CH:62]/[C:63]([O:65][C:66]([CH3:67])([CH3:68])[CH3:69])=[O:64])=[C:50]([N:52]5[CH2:57][CH2:56][CH2:55][CH:54]([OH:58])[CH2:53]5)[N:51]=[C:46]4[CH:45]=3)=[O:43])[S:39][CH:40]=2)[CH2:35][CH2:34][CH2:33]1

Participants

3

Reactant 2

HCID 86588104tert-Butyl (E)-3-[8-{[(4-cyclobutyl-1,3-thiazol-2-yl)amino]carbonyl}-2-(3-formyloxy-piperidino)-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl]-2-propenoateHCID 136347719tert-Butyl (E)-3-{2-hydroxy-8-[(4-isopropyl-1,3-thiazol-2-yl)methoxy]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoate

Product 1

HCID 86588105tert-Butyl (E)-3-[8-{[(4-cyclobutyl-1,3-thiazol-2-yl)amino]carbonyl}-2-(3-hydroxy-piperidino)-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl]-2-propenoate

Procedure

Reactions were performed in the same manner as in Example 1, (K) by using tert-butyl (E)-3-[8-{[(4-cyclobutyl-1,3-thiazol-2-yl)amino]carbonyl}-2-(3-formyloxy-piperidino)-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl]-2-propenoate (35 mg, 0.060 mmol), and the resulting crude crystals were purified by thin layer silica gel chromatography (chloroform:methanol=40:1) to obtain 16 mg (40% for the two steps) of the title compound as yellow crystals.

Workup

  1. customthe resulting crude crystals were purified by thin layer silica gel chromatography (chloroform:methanol=40:1)

Sources & evidence

ORD record
ord-e1d067dff2984da4955c7190d7f44706
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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