tert-Butyl (E)-3-{8-({[4-(tert-butyl)-1,3-thiazol-2-yl]amino}carbonyl)-2-[(3R)-3-formyloxyhexahydro-1-pyridinyl]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoate → tert-Butyl (E)-3-{8-({[4-(tert-butyl)-1,3-thiazol-2-yl]amino}carbonyl)-2-[(3R)-3-hydroxyhexahydro-1-pyridinyl]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoate

HRID 1828467Notes

Reaction equation

HRID 1828467 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.[C:32]([C:36]1[N:37]=[C:38]([NH:41][C:42]([C:44]2[CH:72]=[CH:71][N:47]3[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]4[CH2:57][CH2:56][CH2:55][C@@H:54]([O:58]C=O)[CH2:53]4)[N:51]=[C:46]3[CH:45]=2)=[O:43])[S:39][CH:40]=1)([CH3:35])([CH3:34])[CH3:33]>>[C:32]([C:36]1[N:37]=[C:38]([NH:41][C:42]([C:44]2[CH:72]=[CH:71][N:47]3[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]4[CH2:57][CH2:56][CH2:55][C@@H:54]([OH:58])[CH2:53]4)[N:51]=[C:46]3[CH:45]=2)=[O:43])[S:39][CH:40]=1)([CH3:35])([CH3:33])[CH3:34]

Participants

3

Reactant 2

HCID 86588108tert-Butyl (E)-3-{8-({[4-(tert-butyl)-1,3-thiazol-2-yl]amino}carbonyl)-2-[(3R)-3-formyloxyhexahydro-1-pyridinyl]-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 86588109tert-Butyl (E)-3-{8-({[4-(tert-butyl)-1,3-thiazol-2-yl]amino}carbonyl)-2-[(3R)-3-hydroxyhexahydro-1-pyridinyl]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoateYield 69.2%

Procedure

Reactions were performed in the same manner as in Example 1, (K) by using tert-butyl (E)-3-{8-({[4-(tert-butyl)-1,3-thiazol-2-yl]amino}carbonyl)-2-[(3R)-3-formyloxyhexahydro-1-pyridinyl]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoate (559 mg, 0.961 mmol) to obtain 368 mg (69%) of the title compound as an orange oily substance.

Sources & evidence

ORD record
ord-20e80e6730594fc0a9dcad40137ac494
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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