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

HRID 1750696ノート

反応式

HRID 1750696 の反応式
[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

参加物

7

反応物 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 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-2cc150dd39d6417e8bd41b2c1e9abe6c
出典データセット
uspto-grants-2015_10
特許番号
US09156829B2

反応ノート

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