1-(2-N-Boc-aminoethyl)piperazine → 6-{[(2-[1-[3-fluoro-6-(methyloxy)-4-quinolinyl]-4-hydroxy-4-piperidinyl]ethyl)amino]methyl}-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

HRID 1787700Notes

Reaction equation

HRID 1787700 reaction equation
[OH:1][C:2]1([CH2:8][CH2:9][NH:10][C:11](=O)OC(C)(C)C)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.N1(CCNC(=O)OC(C)(C)C)CCNCC1.Br[C:35]1[C:44]2[C:39](=[CH:40][CH:41]=[C:42]([O:45][CH3:46])[CH:43]=2)[N:38]=[CH:37][C:36]=1[F:47].BrC1C(F)=CN=C2C=1N=C(OC)C=C2.[O:62]=[C:63]1[CH2:68][O:67][C:66]2[CH:69]=[CH:70][C:71](C=O)=[N:72][C:65]=2[NH:64]1.O=C1CSC2C=CC(C=O)=NC=2N1>>[F:47][C:36]1[CH:37]=[N:38][C:39]2[C:44]([C:35]=1[N:5]1[CH2:4][CH2:3][C:2]([CH2:8][CH2:9][NH:10][CH2:11][C:71]3[CH:70]=[CH:69][C:66]4[O:67][CH2:68][C:63](=[O:62])[NH:64][C:65]=4[N:72]=3)([OH:1])[CH2:7][CH2:6]1)=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=2

Participants

7

Reactant 6

HCID 15144011-(2-N-Boc-aminoethyl)piperazineHCID 115935913-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carbaldehydeHCID 218737373-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehydeHCID 224695294-Bromo-3-fluoro-6-methoxyquinolineHCID 454803208-Bromo-7-fluoro-2-methoxy-1,5-naphthyridineHCID 57599589tert-butyl N-[2-(4-hydroxypiperidin-4-yl)ethyl]carbamate

Product 1

HCID 115620746-{[(2-[1-[3-fluoro-6-(methyloxy)-4-quinolinyl]-4-hydroxy-4-piperidinyl]ethyl)amino]methyl}-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-oneYield 26.1%

Procedure

The title compound (71 mg, 26%) was prepared as a yellow solid according to Example 1, except substituting the following three reagents: 1,1-dimethylethyl [2-(4-hydroxy-4-piperidinyl)ethyl]carbamate (1.5 g, 6.15 mmol) [prepared according to Example 20] for 1,1-dimethylethyl [2-(1-piperazinyl)ethyl]carbamate, 4-bromo-3-fluoro-6-(methyloxy)quinoline (1.57 g, 6.15 mmol) for 8-bromo-7-fluoro-2-(methyloxy)-1,5-naphthyridine and 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehyde (100 mg, 0.564 mmol) for 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carbaldehyde: LCMS (ES) m/e 482 (M+H)+; 1H NMR (400 MHz, CD3OD) δ 8.47 (d, J=4.6 Hz, 1H), 7.87 (d, J=9.1 Hz, 1H), 7.39 (d, J=2.7 Hz, 1H), 7.33 (dd, J=2.7, 6.3 Hz, 1H), 7.28 (d, J=8.0 Hz, 1H), 6.99 (d, J=8.0 Hz, 1H), 4.65 (s, 2H), 3.96 (s, 3H), 3.81 (s, 3H), 3.55-3.61 (m, 2H), 3.26-3.29 (m, 2H), 2.88-2.91 (m, 2H), 1.80-1.93 (m, 6H).

Sources & evidence

ORD record
ord-7ce3a00dab6444358b2c2894e3b68f80
Source dataset
uspto-grants-2009_03
Patent number
US07511035B2

Reaction notes

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