Triethylamine → 2-(7-acetyl-1H-benzimidazol-1-yl)-N-{1-[4-(1-cyano-1-methylethyl)phenyl]ethyl}acetamide

HRID 419988Notes

Reaction equation

HRID 419988 reaction equation
[C:1]([C:4]1[C:9]2[N:10]([CH2:13][C:14]([OH:16])=O)[CH:11]=[N:12][C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[NH2:17][CH:18]([C:20]1[CH:25]=[CH:24][C:23]([C:26]([CH3:30])([CH3:29])[C:27]#[N:28])=[CH:22][CH:21]=1)[CH3:19].CCN(CC)CC.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CC#N.O>[C:1]([C:4]1[C:9]2[N:10]([CH2:13][C:14]([NH:17][CH:18]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([C:27]#[N:28])([CH3:29])[CH3:30])=[CH:22][CH:21]=3)[CH3:19])=[O:16])[CH:11]=[N:12][C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 582984592-[4-(1-Aminoethyl)phenyl]-2-methylpropanenitrileHCID 58298480(7-acetyl-1H-benzimidazol-1-yl)acetic acid

Product 1

HCID 248501222-(7-acetyl-1H-benzimidazol-1-yl)-N-{1-[4-(1-cyano-1-methylethyl)phenyl]ethyl}acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

2-(7-acetyl-1H-benzimidazol-1-yl)-N-{1-[4-(1-cyano-1-methylethyl)phenyl]ethyl}acetamide is synthesized according to example 5 by mixing 7-acetyl-1H-benzimidazol-1-ylacetic acid (90.0 mg, 0.413 mmol) prepared according to scheme 4, 2-[4-(1-aminoethyl)phenyl]-2-methylpropanenitrile (77.6 mg, 0.413 mmol) prepared according to scheme 6 and Et3N (125 mg, 1.24 mmol, 0.173 mL) and HATU (157 mg, 0.413 mmol) in dry MeCN (10.0 mL). The product is purified by reverse phase HPLC: Gilson prep pumps; Flow rate: 30 ml/min; Column: Synergi Polar (4μ) 21.2×50 mm; Mobile phase: A=water (0.05% TFA) B=MeCN (49.5 mg, 0.128 mmol, 31.0%). 1H NMR (400 MHz, DMSO-D6) δ ppm 1.35 (d, J=7.03 Hz, 3H) 1.66 (s, 6H) 2.38 (s, 3H) 4.74-4.87 (m, J=7.23, 7.23 Hz, 1H) 5.14 (s, 2H) 7.26 (t, J=7.81 Hz, 1H) 7.35 (d, J=8.40 Hz, 2H) 7.45 (d, J=8.40 Hz, 2H) 7.71 (d, J=7.62 Hz, 1H) 7.85 (d, J=8.01 Hz, 1H) 8.21 (s, 1H) 8.65 (d, J=7.81 Hz, 1H); MS [M+H] calcd.: 389.19. found: 389.09.

Workup

  1. customprepared
  2. customprepared
  3. customThe product is purified by reverse phase HPLC

Sources & evidence

ORD record
ord-284b9be53cc8473fbc08897cf641b634
Source dataset
uspto-grants-2012_01
Patent number
US08093402B2

Reaction notes

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