(2S)-2-Amino-2-phenylacetamide--hydrogen chloride (1/1) → (S)-N-(2-amino-2-oxo-1-phenylethyl)-N3(4-(2-aminopyridin-4-yloxy)-3-fluorophenyl)malonamide, hydrochloride salt

HRID 2237280

Reaction equation

HRID 2237280 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:21])[CH2:17][C:18]([OH:20])=O)=[CH:11][C:10]=2[F:22])[CH:5]=[CH:4][N:3]=1.[ClH:23].[NH2:24][C@@H:25]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:26]([NH2:28])=[O:27]>>[ClH:23].[NH2:28][C:26](=[O:27])[C@@H:25]([NH:24][C:18](=[O:20])[CH2:17][C:16]([NH:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[CH:7]=2)=[C:10]([F:22])[CH:11]=1)=[O:21])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

3

Reactant 2

HCID 22850726(2S)-2-Amino-2-phenylacetamide--hydrogen chloride (1/1)HCID 598528453-(4-(2-Aminopyridin-4-yloxy)-3-fluorophenylamino)-3-oxopropanoic acid

Product 1

HCID 131727213(S)-N-(2-amino-2-oxo-1-phenylethyl)-N3(4-(2-aminopyridin-4-yloxy)-3-fluorophenyl)malonamide, hydrochloride saltYield 53%

Procedure

3-(4-(2-Aminopyridin-4-yloxy)-3-fluorophenylamino)-3-oxopropanoic acid (30 mg, 0.10 mmol) was coupled with (S)-2-amino-2-phenylacetamide hydrochloride (Acros, 28 mg, 0.15 mmol) in a manner similar to that which is described in Step C of Example 1 to give (S)—N1-(2-amino-2-oxo-1-phenylethyl)-N3-(4-(2-aminopyridin-4-yloxy)-3-fluorophenyl)malonamide, hydrochloride salt (25 mg, 53% yield). 1H NMR (DMSO-d6) δ 10.68 (s, 1H), 8.80 (d, 1H, J=8.0 Hz), 7.96 (d, 1H, J=7.5 Hz), 7.77-7.90 (m, 4H), 7.20-7.45 (m, 8H), 6.70 (m, 1H), 6.12 (s, 1H), 5.39 (d, 1H, J=7.5 Hz), 3.48 (d, 1H, J=15.0 Hz), 3.41 (d, 1H, J=15.0 Hz); MS(ESI+) m/z 438.26 (M+H)+.

Sources & evidence

ORD record
ord-ce33b4ff54d04754b57e15985167e467
Source dataset
uspto-grants-2010_05
Patent number
US07714138B2

Linked notes

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