Cyclopentylamine → N1-(4-(2-aminopyridin-4-yloxy)-3-fluorophenyl)-N3-cyclopentylmalonamide, hydrochloride salt

HRID 2237284Notes

Reaction equation

[ClH:1].NC(=O)[C@@H:4]([NH:11][C:12](=[O:32])[CH2:13][C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]2[CH:29]=[CH:28][N:27]=[C:26]([NH2:30])[CH:25]=2)=[C:19]([F:31])[CH:18]=1)=[O:15])[C:5]1C=C[CH:8]=[CH:7][CH:6]=1.C1(N)CCCC1>>[ClH:1].[NH2:30][C:26]1[CH:25]=[C:24]([O:23][C:20]2[CH:21]=[CH:22][C:17]([NH:16][C:14](=[O:15])[CH2:13][C:12]([NH:11][CH:4]3[CH2:5][CH2:6][CH2:7][CH2:8]3)=[O:32])=[CH:18][C:19]=2[F:31])[CH:29]=[CH:28][N:27]=1

Participants

Reactant 2

HCID 2906Cyclopentylamine

HCID 131727213(S)-N-(2-amino-2-oxo-1-phenylethyl)-N3(4-(2-aminopyridin-4-yloxy)-3-fluorophenyl)malonamide, hydrochloride salt2×

Product 1

HCID 131727215N1-(4-(2-aminopyridin-4-yloxy)-3-fluorophenyl)-N3-cyclopentylmalonamide, hydrochloride saltYield 44%

Procedure

3-(4-(2-Aminopyridin-4-yloxy)-3-fluorophenylamino)-3-oxopropanoic acid (Compound C of Example 102, 30 mg, 0.10 mmol) was coupled with cyclopentanamine (Aldrich, 17 mg, 0.2 mmol) in a manner similar to that which is described in Step C of Example 1 to give N1-(4-(2-aminopyridin-4-yloxy)-3-fluorophenyl)-N3-cyclopentylmalonamide, hydrochloride salt (18 mg, 44% yield). 1H NMR (DMSO-d6) δ 13.34 (s, 1H), 10.66 (s, 1H), 8.15 (d, 1H, J=7.0 Hz), 7.96 (d, 1H, J=7.0 Hz), 7.77-7.88 (m, 3H), 7.42 (m, 2H), 6.70 (d, 1H, J=7.5 Hz), 6.12 (s, 1H), 3.98 (m, 1H), 3.69 (s, 2H), 1.78 (m, 2H), 1.63 (m, 2H), 1.49 (m, 2H), 1.37 (m, 2H); MS(ESI+) m/z 373.30 (M+H)+.

Sources & evidence

ORD record: ord-bf0a3d51ec4a4d60baa0b130411e0613
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07714138B2

Reaction notes

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