4-Pyridinemethanamine → HCID 58882895, compound

HRID 2364136Notes

Reaction equation

[CH2:1]([C:8]1[CH:17]=[C:16]2[C:11]([C:12]([OH:35])=[C:13]([C:30]([O:32]CC)=O)[C:14](=[O:29])[N:15]2[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)=[N:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:36][CH2:37][C:38]1[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=1>CCO>[CH2:1]([C:8]1[CH:17]=[C:16]2[C:11]([C:12]([OH:35])=[C:13]([C:30]([NH:36][CH2:37][C:38]3[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=3)=[O:32])[C:14](=[O:29])[N:15]2[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)=[N:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of ethyl 7-benzyl-4-hydroxy-1-[4-(methylsulfonyl)benzyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (40 mg, 0.080 mmol) and 4-(aminomethyl)pyridine (122 μL, 1.2 mmol) in EtOH (1 mL) was heated at 120° C. in a sealed tube in a microwave for 30 min. The reaction mixture was concentrated at reduced pressure, reconstituted in CH2Cl2 and washed with a mixture of 1N HCl and brine. Drying and evaporation of the organic phase gave the product as a pale green solid: 1H NMR (CDCl3) δ 10.81 (1H, br t, J=6 Hz), 8.69 (2H, d, J=7 Hz), 8.65 (1H, d, J=1 Hz), 7.83 (2H, d, J=8 Hz), 7.76 (2H, d, J=6 Hz), 7.31 (3H, m), 7.19 (2H, d, J=8 Hz), 7.11 (1H, s), 7.03 (2H, m), 5.43 (2H, br s), 4.86 (2H, d, J=6 Hz), 4.08 (2H, s), 3.03 (3H, s); HRMS calcd for C30H26N4O5S+H+: 555.1702. Found: 555.1699.

Workup

concentrationThe reaction mixture was concentrated at reduced pressure
washwashed with a mixture of 1N HCl and brine
customDrying
customevaporation of the organic phase

Sources & evidence

ORD record: ord-a9545714a42f420783a583d4ae40cfac
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691991B2

Reaction notes

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