1-Pyrrolidineethanamine → HCID 58168256, compound

HRID 1029293Notes

Reaction equation

Cl[C:2]1[CH:16]=[CH:15][C:5]2[C:6](=[O:14])[NH:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[CH:12][CH:11]=[CH:10][N:9]=3.[N:17]1([CH2:22][CH2:23][NH2:24])[CH2:21][CH2:20][CH2:19][CH2:18]1>>[N:17]1([CH2:22][CH2:23][NH:24][C:2]2[CH:16]=[CH:15][C:5]3[C:6](=[O:14])[NH:7][C:8]4[C:13]([C:4]=3[CH:3]=2)=[CH:12][CH:11]=[CH:10][N:9]=4)[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

Reactant 2

HCID 13441-Pyrrolidineethanamine

HCID 581682989-chloro-5H-benzo[c][1,8]naphthyridin-6-one

Product 1

HCID 58168256HCID 58168256, compoundYield 18.1%

Procedure

The title compound was synthesized according to the procedure described for the preparation of Example 456 using 6 (100 mg, 0.43 mmol) and 2-pyrrolidin-1-ylethanamine (0.22 mL, 1.73 mmol) to provide 474 (24 mg, 18% yield) as a white powder. LC-MS (M+H=309, obsd.=309). 1H NMR (400 MHz, DMSO-D6) δ 11.59 (s, 1H), 9.65 (s, 1H), 8.75 (d, J=8.0, 1H), 8.39 (m, 1H), 8.05 (d, J=8.7, 1H), 7.42 (s, 1H), 7.28 (dd, J=4.6, 7.9, 1H), 6.95 (d, J=8.7, 1H), 3.65 (s, 4H), 3.41 (s, 2H), 3.10 (s, 2H), 1.96 (d, J=59.8, 4H).

Workup

customThe title compound was synthesized

Sources & evidence

ORD record: ord-f86193d164d540f4b22bb20e79fd48e5
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735584B2

Reaction notes

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