5-Fluoro-2-(pyrimidin-2-yl)benzoic acid → 5-Fluoro-N-[(1S,2S)-2-{[3-methyl-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-2-(pyrimidin-2-yl)benzamide

HRID 1750647Notes

Reaction equation

HRID 1750647 reaction equation
[CH3:1][C:2]1[C:3]([NH:12][C@H:13]2[CH2:17][CH2:16][CH2:15][C@@H:14]2[NH:18][C:19](C2C(N3N=CC=N3)=CC=CN=2)=[O:20])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:7]=1.Cl.CN(C1C=NC(C(F)(F)F)=CN=1)[C@H]1CCC[C@@H]1N.[F:51][C:52]1[CH:53]=[CH:54][C:55]([C:61]2[N:66]=[CH:65][CH:64]=[CH:63][N:62]=2)=[C:56]([CH:60]=1)C(O)=O>>[F:51][C:52]1[CH:60]=[CH:56][C:55]([C:61]2[N:62]=[CH:63][CH:64]=[CH:65][N:66]=2)=[C:54]([CH:53]=1)[C:19]([NH:18][C@H:14]1[CH2:15][CH2:16][CH2:17][C@@H:13]1[NH:12][C:3]1[C:2]([CH3:1])=[N:7][C:6]([C:8]([F:10])([F:9])[F:11])=[CH:5][N:4]=1)=[O:20]

Participants

4

Reactant 3

HCID 670869505-Fluoro-2-(pyrimidin-2-yl)benzoic acidHCID 118308127(1S,2S)-1-N-Methyl-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride2×HCID 118308165N-[(1S,2S)-2-{[3-Methyl-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-3-(2H-1,2,3-triazol-2-yl)pyridine-2-carboxamide

Product 1

HCID 1183082295-Fluoro-N-[(1S,2S)-2-{[3-methyl-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-2-(pyrimidin-2-yl)benzamide

Procedure

Prepared according to the procedure for N-[(1S,2S)-2-{ [3-methyl-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-3-(2H-1,2,3-triazol-2-yl)pyridine-2-carboxamide (Example 76) from (1S,2S)-1-N-methyl-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride (Intermediate 23; 60 mg, 0.20 mmol) and 5-fluoro-2-(pyrimidin-2-yl)benzoic acid (CAS number 1293284-57-7; 41 mg, 0.20 mmol) except this was purified only by column chromatography (silica, 0 to 100% ethyl acetate/petrol) to afford the title compound.

Workup

  1. customPrepared
  2. customthis was purified only by column chromatography (silica, 0 to 100% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-9ef0b6dc854c4452ab9f3a9f6d6d566b
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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