(S)-3-[(5-amino-pyridine-3-carbonyl)-amino]-tetrahydrofuran-3-carboxylic acid → (S)-5-amino-N-{3-[2-fluoro-4-(4-methoxy-2-trifluoromethyl-phenylamino)-benzyl-carbamoyl]-tetrahydro-furan-3-yl}-nicotinamide

HRID 1428209Notes

Reaction equation

HRID 1428209 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]([NH:10][C@@:11]2([C:16]([OH:18])=O)[CH2:15][CH2:14][O:13][CH2:12]2)=[O:9])[CH:5]=[N:6][CH:7]=1.[F:19][C:20]1[CH:27]=[C:26]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][C:30]=2[C:37]([F:40])([F:39])[F:38])[CH:25]=[CH:24][C:21]=1[CH2:22][NH2:23]>>[NH2:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([CH:3]=1)[C:8]([NH:10][C@@:11]1([C:16](=[O:18])[NH:23][CH2:22][C:21]2[CH:24]=[CH:25][C:26]([NH:28][C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][C:30]=3[C:37]([F:38])([F:39])[F:40])=[CH:27][C:20]=2[F:19])[CH2:15][CH2:14][O:13][CH2:12]1)=[O:9]

Participants

3

Reactant 2

HCID 59496422(S)-3-[(5-amino-pyridine-3-carbonyl)-amino]-tetrahydrofuran-3-carboxylic acidHCID 667658162-Fluoro-4-(4-methoxy-2-trifluoromethyl-phenylamino)-benzylamine

Product 1

HCID 56840393(S)-5-amino-N-{3-[2-fluoro-4-(4-methoxy-2-trifluoromethyl-phenylamino)-benzyl-carbamoyl]-tetrahydro-furan-3-yl}-nicotinamideYield 27%

Procedure

Analogously to Example 1e), (S)-3-[(5-amino-pyridine-3-carbonyl)-amino]-tetrahydrofuran-3-carboxylic acid (0.55 mmol) was reacted with 2-fluoro-4-(4-methoxy-2-trifluoromethyl-phenylamino)-benzylamine (0.55 mMol, from 1b). The product was obtained in a yield of 27% of theory.

Workup

  1. customThe product was obtained in a yield of 27% of theory

Sources & evidence

ORD record
ord-b1b796bb05524b9688d65dea83b007ba
Source dataset
uspto-grants-2015_01
Patent number
US08937073B2

Reaction notes

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