Triethylamine → (-)-N-{1-[4-(1-Cyano-1-ethylpropyl)phenyl]ethyl}-2-(6,7-difluoro-1H-benzimidazol-1-yl)acetamide

HRID 603146ノート

反応式

HRID 603146 の反応式
[NH2:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH2:15][CH3:16])([CH2:13][CH3:14])[C:11]#[N:12])=[CH:6][CH:5]=1)[CH3:3].[F:17][C:18]1[CH:19]=[CH:20][C:21]2[N:25]=[CH:24][N:23]([CH2:26][C:27](O)=[O:28])[C:22]=2[C:30]=1[F:31].CCN(CC)CC.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[OH-].[Na+]>CC#N.O>[C:11]([C:10]([C:7]1[CH:8]=[CH:9][C:4]([CH:2]([NH:1][C:27](=[O:28])[CH2:26][N:23]2[C:22]3[C:30]([F:31])=[C:18]([F:17])[CH:19]=[CH:20][C:21]=3[N:25]=[CH:24]2)[CH3:3])=[CH:5][CH:6]=1)([CH2:13][CH3:14])[CH2:15][CH3:16])#[N:12]

参加物

8

反応物 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57939018HCID 57939018、化合物HCID 582984502-[4-(1-Aminoethyl)phenyl]-2-ethylbutanenitrile

生成物 1

HCID 24850279(-)-N-{1-[4-(1-Cyano-1-ethylpropyl)phenyl]ethyl}-2-(6,7-difluoro-1H-benzimidazol-1-yl)acetamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒2 回

実験手順

2-[4-(1-Aminoethyl)phenyl]-2-ethylbutanenitrile (520 mg, 2.41 mmol) prepared according to scheme 24, (6,7-difluoro-1H-benzimidazol-1-yl)acetic acid (510 mg, 2.41 mmol) prepared according to scheme 2 and Et3N (731 mg, 7.22 mmol, 1.00 mL) are mixed in MeCN (15.0 mL). HATU (915 mg, 2.41 mmol) is added and the mixture is stirred for 2 hours. 1N NaOH (40.0 mL) is added, and the aqueous phase is extracted with EtOAc (4 times 40.0 mL). The combined organic phases are dried with MgSO4, filtered and concentrated on the rotovaporator. The product is purified by HPLC: Gilson prep pumps, Flow rate: 30 ml/min, Column: Gemini (5%) 21.2×50 mm, Mobile phase: A=water (10 mM NH4CO3) B=MeCN, (804 mg, 1.96 mmol, 81%). 1H NMR (400 MHz, DMSO-D6) δ ppm 0.77 (t, J=7.32 Hz, 6H) 1.40 (d, J=7.03 Hz, 3H) 1.83-2.13 (m, 4H) 4.96 (ddd, J=14.65, 7.23, 7.03 Hz, 1H) 5.08 (s, 2H) 7.21 (ddd, J=11.57, 8.93, 7.62 Hz, 1H) 7.35-7.41 (m, 4H) 7.45 (ddd, J=8.84, 3.86, 0.78 Hz, 1H) 8.19-8.22 (m, 1H) 8.83 (d, J=8.01 Hz, 1H); MS [M+H], calcd: 411.0, found: 411.3.

後処理

  1. customprepared
  2. extractionthe aqueous phase is extracted with EtOAc (4 times 40.0 mL)
  3. dry with materialThe combined organic phases are dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated on the rotovaporator
  6. customThe product is purified by HPLC

出典と根拠

ORDレコード
ord-787a74a2196e465bb945c590869f2079
出典データセット
uspto-grants-2011_03
特許番号
US07906654B2

反応ノート

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