2-Pyridinamine, N-methyl- → HCID 69586871, compound

HRID 723212Notes

Reaction equation

HRID 723212 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1NC.C[CH2:10][N:11](C(C)C)C(C)C.[CH3:18][O:19][C:20]([C:22]1[S:23][C:24]([S:40][CH3:41])=[C:25]([S:27]([C:30]2[CH:35]=[CH:34][C:33](Br)=[C:32]([N+:37]([O-:39])=[O:38])[CH:31]=2)(=[O:29])=[O:28])[CH:26]=1)=[O:21]>C1COCC1>[CH3:18][O:19][C:20]([C:22]1[S:23][C:24]([S:40][CH3:41])=[C:25]([S:27]([C:30]2[CH:35]=[CH:34][C:33]([NH:11][CH2:10][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[C:32]([N+:37]([O-:39])=[O:38])[CH:31]=2)(=[O:29])=[O:28])[CH:26]=1)=[O:21]

Participants

5

Reactant 3

HCID 207272-Pyridinamine, N-methyl-HCID 81531DiisopropylethylamineHCID 69586481HCID 69586481, compound

Product 1

HCID 69586871HCID 69586871, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Pyridin-2-yl-methylamine (60 μL), DIEA (175 μL, 1 mmol), and 4-(4-bromo-3-nitro-benzenesulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester ((Example 264: step b) 56 mg, 0.12 mmol) were heated at 60° C. in THF (3 mL) for 30 min. The solvent was removed in vacuo and the residue was purified by SiO2 flash column chromatography to yield the title compound (41 mg, 69%). 1H-NMR (CDCl3): δ 9.46 (m, 1H), 8.90 (m, 1H), 8.64 (m, 1H), 8.01 (d, 1H, J=2.6 Hz), 7.94 (m, 1H), 8.03 (m, 2H), 7.71 (dt, 1H, J=1.9, 7.7 Hz), 7.28 (m, 2H), 6.95 (d, 1H, J=9.0 Hz), 4.67 (d, 1H, J=5.1 Hz), 3.87 (s, 3H), 2.60 (s, 3).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by SiO2 flash column chromatography

Sources & evidence

ORD record
ord-0bd7f8ad430345c0aeaefd0f14935b1d
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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