HCID 49846267, compound → HCID 49846266, compound

HRID 1926695Notes

Reaction equation

[NH2:1][C@@H:2]1[CH2:11][C:10]2[C:5](=[CH:6][C:7]([Br:12])=[CH:8][CH:9]=2)[N:4]([OH:13])[C:3]1=[O:14].BrC1C=C2C(C[C@H](NC(=O)OC(C)(C)C)C(=O)N2OC(OC(C)(C)C)=O)=CC=1>>[NH2:1][C@H:2]1[CH2:11][C:10]2[C:5](=[CH:6][C:7]([Br:12])=[CH:8][CH:9]=2)[N:4]([OH:13])[C:3]1=[O:14]

Participants

Reactant 2

HCID 49846267HCID 49846267, compound

HCID 59627036HCID 59627036, compound

Product 1

HCID 49846266HCID 49846266, compound

Procedure

Following the procedure for the preparation of (3R)-3-amino-7-bromo-1-hydroxy-3,4-dihydroquinolin-2(1H)-one (29) in Example 5 but using tert-butyl {(3S)-7-bromo-1-[(tert-butoxycarbonyl)oxy]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}carbamate (28) as starting material, the title product was obtained as a white powder (23 mg, 62%). LCMS m/z 258.9 (M+1). 1H NMR (500 MHz, DMSO-d6) δ 2.70 (br dd, J=15.6, 12.7 Hz, 1H) 2.99 (dd, J=15.6, 6.1 Hz, 1H), 3.52 (dd, J=12.7, 6.0 Hz, 1H), 7.16-7.20 (m, 2H), 7.28 (d, J=1.6 Hz, 1H).

Sources & evidence

ORD record: ord-fff2fe216434400fb56f0e75ef242774
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183238B2

Reaction notes

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