N,N-Diethyl-2-propanamine → (S)-1-(3-fluorophenyl)-N-(1-(imidazo[1,2-a]pyrazin-8-yl)pyrrolidin-3-yl)-1H-1,2,4-triazole-3-carboxamide

HRID 1755270ノート

反応式

HRID 1755270 の反応式
Cl.[N:2]1[CH:3]=[CH:4][N:5]2[CH:10]=[CH:9][N:8]=[C:7]([N:11]3[CH2:15][CH2:14][C@H:13]([NH2:16])[CH2:12]3)[C:6]=12.[F:17][C:18]1[CH:19]=[C:20]([N:24]2[CH:28]=[N:27][C:26]([C:29](O)=[O:30])=[N:25]2)[CH:21]=[CH:22][CH:23]=1.C(N(CC)C(C)C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C>[F:17][C:18]1[CH:19]=[C:20]([N:24]2[CH:28]=[N:27][C:26]([C:29]([NH:16][C@H:13]3[CH2:14][CH2:15][N:11]([C:7]4[C:6]5[N:5]([CH:4]=[CH:3][N:2]=5)[CH:10]=[CH:9][N:8]=4)[CH2:12]3)=[O:30])=[N:25]2)[CH:21]=[CH:22][CH:23]=1

参加物

7

反応物 4

HCID 521913N,N-Diethyl-2-propanamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866882381-(3-fluorophenyl)-1H-1,2,4-triazole-3-carboxylic acidHCID 86720541(5)-1-(Imidazo[1,2-a]pyrazin-8-yl)pyrrolidin-3-amine hydrochloride salt

生成物 1

HCID 75202691(S)-1-(3-fluorophenyl)-N-(1-(imidazo[1,2-a]pyrazin-8-yl)pyrrolidin-3-yl)-1H-1,2,4-triazole-3-carboxamide収率 75%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a suspension of (S)-1-(imidazo[1,2-a]pyrazin-8-yl)pyrrolidin-3-amine hydrochloride salt (84 mg, 0.3 mmol) and 1-(3-fluorophenyl)-1H-1,2,4-triazole-3-carboxylic acid (63 mg, 0.3 mmol) in DMF (5 mL) was added diethylisopropyl amine (650 mg, 5 mmol), followed by HATU (120 mg, 0.31 mmol). The resulting solution was stirred at room temperature for 1 h. The reaction mixture was diluted with ethyl acetate and washed with saturated aqueous solutions of KH2PO4 and NaHCO3, followed by brine. The organic layer was concentrated in vacuo and the residue purified by reverse phase HPLC (acetonitrile-H2O with 0.1% TFA as eluent) to give 88 mg of the title compound (75% yield) as a white solid.

後処理

  1. washwashed with saturated aqueous solutions of KH2PO4 and NaHCO3
  2. concentrationThe organic layer was concentrated in vacuo
  3. customthe residue purified by reverse phase HPLC (acetonitrile-H2O with 0.1% TFA as eluent)

出典と根拠

ORDレコード
ord-1b7506809213495d8c48cf13ee41a72c
出典データセット
uspto-grants-2015_10
特許番号
US09169261B2

反応ノート

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