HCID 68576907, compound → HCID 59026142, compound

HRID 639074Notes

Reaction equation

HRID 639074 reaction equation
[CH:1]([C:3]1[C:4]([F:16])=[CH:5][N:6]=[C:7]2[C:12]=1[N:11]=[C:10]([O:13][CH3:14])[CH:9]=[C:8]2F)=[CH2:2].[NH:17]1[CH2:21][CH2:20][C@H:19]([CH2:22][NH:23][CH2:24][C:25]2[CH:26]=[CH:27][C:28]3[O:29][CH2:30][C:31](=[O:35])N[C:33]=3[N:34]=2)[CH2:18]1>>[O:35]1[C:27]2[CH:26]=[C:25]([CH2:24][NH:23][CH2:22][C@@H:19]3[CH2:20][CH2:21][N:17]([CH2:2][CH2:1][C:3]4[C:12]5[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[N:11]=5)[N:6]=[CH:5][C:4]=4[F:16])[CH2:18]3)[N:34]=[CH:33][C:28]=2[O:29][CH2:30][CH2:31]1

Participants

3

Reactant 2

HCID 68576907HCID 68576907, compoundHCID 68577458HCID 68577458, compound

Product 1

HCID 59026142HCID 59026142, compound

Procedure

Prepared essentially according to the procedure for Example 22, except substituting 8-ethenyl-7-fluoro-2-(methyloxy)-1,5-naphthyridine (143 mg, 0.70 mmole) for 8-ethenyl-4,7-difluoro-2-(methyloxy)-1,5-naphthyridine, and substituting 2,3-dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehyde (115 mg, 0.70 mmole) for 6-({[(3S)-3-pyrrolidinylmethyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one, the title compound was prepared as an orange hygroscopic solid: LC/MS (ES) m/e 454 (M+H)+; 1H NMR (DMSO, 400 MHz) δ 9.8 (bs, 1H), 8.85 (s, 1H), 8.4 (d, J=5.6 Hz, 1H), 8.33 (d, J=9.1 Hz, 1H), 7.51 (d, J=11.6 Hz, 1H), 7.29 (d, J=9.1 Hz, 1H), 4.5 (m, 3H), 4.25 (s, 2H), 4.1 (s, 3H), 3.8 (m, 1H), 3.7 (m, 2H), 3.6 (m, 2H), 3.5 (m, 2H), 3.25 (m, 2H), 3.1 (s, 2H), 2.85 (m, 2H), 2.25 (m, 1H), 1.8 (m, 1H), 1.3 (s, 1H), 0.8 (m, 1H).

Workup

  1. customPrepared essentially

Sources & evidence

ORD record
ord-199e7bea702146df883f444f692e5982
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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