Neopentylamine → N1-(4-(2-aminopyridin-4-yloxy)-3-fluorophenyl)-N3-neopentylmalonamide, hydrochloride salt

HRID 2374066Notes

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]1[CH:10]=CC=C[CH:6]=1.[CH3:34]C(C)(C)CN>>[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][CH2:4][C:5]([CH3:10])([CH3:34])[CH3:6])=[O:32])=[CH:18][C:19]=2[F:31])[CH:29]=[CH:28][N:27]=1

Participants

Reactant 2

HCID 79882Neopentylamine

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

Product 1

HCID 131727217N1-(4-(2-aminopyridin-4-yloxy)-3-fluorophenyl)-N3-neopentylmalonamide, hydrochloride saltYield 32%

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 2,2-dimethylpropan-1-amine (Aldrich, 12 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-neopentylmalonamide, hydrochloride salt (13 mg, 32% yield). 1H NMR (DMSO-d6) δ 13.34 (s, 1H), 10.69 (s, 1H), 8.08 (m, 1H), 7.96 (d, 1H, J=7.0 Hz), 7.87 (m, 3H), 7.44 (m, 2H), 6.70 (m, 1H), 6.13 (d, 1H, J=2.0 Hz), 3.34 (s, 2H), 2.91 (d, 2H, J=6.5 Hz), 0.84 (s, 9H); MS(ESI+) m/z 375.32 (M+H)+.

Sources & evidence

ORD record: ord-82a732dce0e84cb097491b97cf5bace9
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459562B2

Reaction notes

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