Cyclopropanemethanamine → HCID 58882922, compound

HRID 2364133Notes

Reaction equation

[CH2:1]([C:8]1[CH:17]=[C:16]2[C:11]([C:12]([OH:24])=[C:13]([C:19]([O:21]CC)=O)[C:14](=[O:18])[NH:15]2)=[N:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:25]1([CH2:28][NH2:29])[CH2:27][CH2:26]1>>[CH2:1]([C:8]1[CH:17]=[C:16]2[C:11]([C:12]([OH:24])=[C:13]([C:19]([NH:29][CH2:28][CH:25]3[CH2:27][CH2:26]3)=[O:21])[C:14](=[O:18])[NH:15]2)=[N:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 75646Cyclopropanemethanamine

HCID 54729996HCID 54729996, compound

Product 1

HCID 58882922HCID 58882922, compound

Procedure

Ethyl 7-benzyl-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate was treated with cyclopropylmethyl amine in a manner similar to that described in Example 2. The product was obtained as a white solid: 1H NMR (d6-DMSO) δ 11.85 (1H, br), 10.85 (1H, br), 10.11 (1H, br),8.20 (1H, br m), 7.39-7.25 (6H, br m), 4.01 (2H, br s), 3.33-3.13 (2H, br m), 1.20-0.90 (1H, m), 0.44 (2H, m), 0.19 (2H, m); HRMS calcd for C20H19N3O3+H+: 350.1505. Found: 350.1517.

Workup

customThe product was obtained as a white solid

Sources & evidence

ORD record: ord-e253aab01c1e42b99f364f73e29863c4
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691991B2

Reaction notes

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