Diisopropylethylamine → N-[(1S,2S)-2-{[3-Methyl-5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]-3-(pyrimidin-2-yl)pyridine-2-carboxamide

HRID 1750696Notes

Reaction equation

HRID 1750696 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C:7]1[C:8]([C:13]([OH:15])=O)=[N:9][CH:10]=[CH:11][CH:12]=1.CCN(C(C)C)C(C)C.Cl.[CH3:26][C:27]1[C:28]([NH:37][C@H:38]2[CH2:42][CH2:41][CH2:40][C@@H:39]2[NH2:43])=[N:29][CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl.C(#N)C>[CH3:26][C:27]1[C:28]([NH:37][C@H:38]2[CH2:42][CH2:41][CH2:40][C@@H:39]2[NH:43][C:13]([C:8]2[C:7]([C:2]3[N:1]=[CH:6][CH:5]=[CH:4][N:3]=3)=[CH:12][CH:11]=[CH:10][N:9]=2)=[O:15])=[N:29][CH:30]=[C:31]([C:33]([F:34])([F:35])[F:36])[CH:32]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 593636623-(Pyrimidin-2-yl)pyridine-2-carboxylic acidHCID 118308266(1S,2S)-1-N-[3-Methyl-5-(trifluoromethyl)pyridin-2-yl]cyclopentane-1,2-diamine hydrochloride2×

Product 1

HCID 118308296N-[(1S,2S)-2-{[3-Methyl-5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]-3-(pyrimidin-2-yl)pyridine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(pyrimidin-2-yl)pyridine-2-carboxylic acid (CAS number 1228431-21-7; 155 mg, 0.77 mmol), DIPEA (0.27 ml, 1.54 mmol) and (1S,2S)-1-N-[3-methyl-5-(trifluoromethyl)pyridin-2-yl]cyclopentane-1,2-diamine hydrochloride (Intermediate 35; 200 mg, 0.68 mmol) in DCM (3 ml) and acetonitrile (5 ml) was added HATU (293 mg, 0.77 mmol). The reaction was stirred at room temperature for 16 hours and then concentrated in vacuo. The residue was purified by reverse phase column chromatography (C18 silica, 0-100% water (0.1% formic acid)/acetonitrile) and then by reverse phase column chromatography (C18 silica, 5-95% water (0.05% ammonia)/acetonitrile) to afford the title compound.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by reverse phase column chromatography (C18 silica, 0-100% water (0.1% formic acid)/acetonitrile) and then by reverse phase column chromatography (C18 silica, 5-95% water (0.05% ammonia)/acetonitrile)

Sources & evidence

ORD record
ord-2cc150dd39d6417e8bd41b2c1e9abe6c
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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