1-Pyrrolidineethanamine → HCID 54703238, compound

HRID 2364182Notes

Reaction equation

[CH2:1]([C:8]1[CH:17]=[C:16]2[C:11]([C:12]([OH:35])=[C:13]([C:30](OCC)=[O:31])[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][CH2:38][N:39]1[CH2:43][CH2:42][CH2:41][CH2:40]1>>[CH2:1]([C:8]1[CH:17]=[C:16]2[C:11]([C:12]([OH:35])=[C:13]([C:30]([NH:36][CH2:37][CH2:38][N:39]3[CH2:43][CH2:42][CH2:41][CH2:40]3)=[O:31])[C:14](=[O:29])[N:15]2[CH2:18][C:19]2[CH:20]=[CH:21][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:23][CH:24]=2)=[N:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 13441-Pyrrolidineethanamine

HCID 58882900HCID 58882900, compound

Product 1

HCID 54703238HCID 54703238, compound

Procedure

This compound was prepared from ethyl 7-benzyl-4-hydroxy-1-[4-(methylsulfonyl)benzyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and N-(2-aminoethyl)pyrrolidine employing methods similar to those described in Example 5 and was obtained as a white solid: 1H NMR (CDCl3) δ 12.80 (1H, br), 10.44 (1H, t, J=6 Hz), 8.60 (1H, d, J=1 Hz), 7.81 (2H, d, J=8.2 Hz), 7.30 (3H, m), 7.19 (2H, d, J=8.2 Hz), 7.06 (1H, s), 7.01 (2H, m), 5.41 (2H, br), 4.05 (2H, s), 4.02 (2H, q, J=6.6 Hz), 3.87 (2H, br), 3.36 (2H, t, J=7 Hz), 3.02 (3H, s), 2.89 (2H, m), 2.24 (2H, br), 2.10 (2H, br); HRMS calcd for C30H32N4O5S+H+: 561.2172. Found: 561.2166.

Workup

customwas obtained as a white solid

Sources & evidence

ORD record: ord-219e6ded9c8e4833af2fb6a004f34d0d
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691991B2

Reaction notes

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