(S)-3-[(5-amino-pyridine-3-carbonyl)-amino]-tetrahydrofuran-3-carboxylic acid → (S)-5-amino-N-(3-{[3-chloro-5-(4-methoxy-2-trifluoromethyl-phenylamino)-pyridin-2-ylmethyl]-carbamoyl}-tetrahydrofuran-3-yl)-nicotinamide

HRID 1428223Notes

Reaction equation

HRID 1428223 reaction equation
[NH2:1][CH2:2][C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=2[C:18]([F:21])([F:20])[F:19])=[CH:5][C:4]=1[Cl:22].[NH2:23][C:24]1[CH:25]=[C:26]([C:30]([NH:32][C@@:33]2([C:38](O)=[O:39])[CH2:37][CH2:36][O:35][CH2:34]2)=[O:31])[CH:27]=[N:28][CH:29]=1>>[NH2:23][C:24]1[CH:29]=[N:28][CH:27]=[C:26]([CH:25]=1)[C:30]([NH:32][C@@:33]1([C:38](=[O:39])[NH:1][CH2:2][C:3]2[C:4]([Cl:22])=[CH:5][C:6]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=3[C:18]([F:21])([F:19])[F:20])=[CH:7][N:8]=2)[CH2:37][CH2:36][O:35][CH2:34]1)=[O:31]

Participants

3

Reactant 2

HCID 59496422(S)-3-[(5-amino-pyridine-3-carbonyl)-amino]-tetrahydrofuran-3-carboxylic acidHCID 66765570(6-Aminomethyl-5-chloro-pyridin-3-yl)-(4-methoxy-2-trifluoromethyl-phenyl)-amine

Product 1

HCID 56840395(S)-5-amino-N-(3-{[3-chloro-5-(4-methoxy-2-trifluoromethyl-phenylamino)-pyridin-2-ylmethyl]-carbamoyl}-tetrahydrofuran-3-yl)-nicotinamide

Procedure

Analogously to Example 1e), (6-aminomethyl-5-chloro-pyridin-3-yl)-(4-methoxy-2-trifluoromethyl-phenyl)-amine (1.3 mmol) was reacted with (S)-3-[(5-amino-pyridin-3-carbonyl)-amino]-tetrahydrofuran-3-carboxylic acid (product from Example 2b, 1.3 mmol).

Sources & evidence

ORD record
ord-1e0ceeb0c1b14117a296b88eade5caf8
Source dataset
uspto-grants-2015_01
Patent number
US08937073B2

Reaction notes

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