3-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carbaldehyde → 6-{[(2-{1-[3-fluoro-6-(methyloxy)-4-quinolinyl]-4-piperidinyl}ethyl)amino]methyl}-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

HRID 2356342Notes

Reaction equation

HRID 2356342 reaction equation
C[C:2]([N:5]([CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)C(=O)[O-])([CH3:4])C.CC(N(CCN1CCNCC1)C(=O)[O-])(C)C.Br[C:34]1[C:43]2[C:38](=[CH:39][CH:40]=[C:41]([O:44][CH3:45])[CH:42]=2)[N:37]=[CH:36][C:35]=1[F:46].BrC1C(F)=CN=C2C=1N=C(OC)C=C2.[O:61]=[C:62]1[CH2:67][O:66][C:65]2[CH:68]=[CH:69]C(C=O)=[N:71][C:64]=2[NH:63]1.O=C1CSC2C=CC(C=O)=NC=2N1>>[F:46][C:35]1[CH:36]=[N:37][C:38]2[C:43]([C:34]=1[N:14]1[CH2:13][CH2:12][CH:11]([CH2:10][CH2:9][NH:5][CH2:2][C:4]3[CH:69]=[CH:68][C:65]4[O:66][CH2:67][C:62](=[O:61])[NH:63][C:64]=4[N:71]=3)[CH2:16][CH2:15]1)=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=2

Participants

7

Reactant 6

HCID 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 53422674Tert-butyl2-(piperazin-1-yl)ethylcarbamateHCID 867611421,1-Dimethylethyl[2-(4-piperidinyl)ethyl]carbamate

Product 1

HCID 115978986-{[(2-{1-[3-fluoro-6-(methyloxy)-4-quinolinyl]-4-piperidinyl}ethyl)amino]methyl}-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-oneYield 33%

Procedure

The title compound (100 mg, 33%) was prepared as a yellow solid according to Example 1, except substituting the following three reagents: 1,1-dimethylethyl[2-(4-piperidinyl)ethyl]carbamate (1 g, 4.38 mmol) [prepared according to Ambler, J.; et. al. Bioorg. Med. Chem. Lett. 1999, 9, 9, 1317.] for 1,1-dimethylethyl[2-(1-piperazinyl)ethyl]carbamate, 4-bromo-3-fluoro-6-(methyloxy)quinoline (2.25 g, 8.77 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 (117 mg, 0.657 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=4.5 Hz, 1H), 7.87 (d, J=9.1 Hz, 1H), 7.40 (d, J=2.7 Hz, 1H), 7.34 (dd, J=2.7, 6.3 Hz, 1H), 7.29 (d, J=8.0 Hz, 1H), 6.99 (d, J=8.0 Hz, 1H), 4.66 (s, 2H), 3.97 (s, 3H), 3.79 (s, 2H), 3.35-3.50 (m, 2H), 3.26-3.30 (m, 2H), 2.71-2.75 (m, 2H), 1.87-1.90 (m, 2H), 1.62-1.66 (m, 3H), 1.52-1.55 (m, 2H).

Sources & evidence

ORD record
ord-28b831804593499ab68c6dfa158ebca7
Source dataset
uspto-grants-2010_07
Patent number
US07759340B2

Reaction notes

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