Triethylamine → 2-(7-Acetyl-1H-benzimidazol-1-yl)-N-{1-[4-(1-cyano-1-methylethyl)-3-fluorophenyl]ethyl}acetamide

HRID 419989Notes

Reaction equation

HRID 419989 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:25]([C:28]1[C:33]2[N:34]([CH2:37][C:38]([OH:40])=O)[CH:35]=[N:36][C:32]=2[CH:31]=[CH:30][CH:29]=1)(=[O:27])[CH3:26].[NH2:41][CH:42]([C:44]1[CH:49]=[CH:48][C:47]([C:50]([CH3:54])([CH3:53])[C:51]#[N:52])=[C:46]([F:55])[CH:45]=1)[CH3:43].CCN(CC)CC>CC#N.O>[C:25]([C:28]1[C:33]2[N:34]([CH2:37][C:38]([NH:41][CH:42]([C:44]3[CH:49]=[CH:48][C:47]([C:50]([C:51]#[N:52])([CH3:54])[CH3:53])=[C:46]([F:55])[CH:45]=3)[CH3:43])=[O:40])[CH:35]=[N:36][C:32]=2[CH:31]=[CH:30][CH:29]=1)(=[O:27])[CH3:26]

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 582984652-[4-(1-Aminoethyl)-2-fluorophenyl]-2-methylpropanenitrileHCID 58298480(7-acetyl-1H-benzimidazol-1-yl)acetic acid

Product 1

HCID 598042642-(7-Acetyl-1H-benzimidazol-1-yl)-N-{1-[4-(1-cyano-1-methylethyl)-3-fluorophenyl]ethyl}acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

2-(7-Acetyl-1H-benzimidazol-1-yl)-N-{1-[4-(1-cyano-1-methylethyl)-3-fluorophenyl]ethyl}acetamide is synthesized according to example 5 by mixing HATU (179 mg, 0.472 mmol), 7-acetyl-1H-benzimidazol-1-ylacetic acid (103 mg, 0.472 mmol) prepared according to scheme 4, 2-[4-(1-aminoethyl)-2-fluorophenyl]-2-methylpropanenitrile (97.0 mg, 0.472 mmol) prepared according to scheme 7 and Et3N (143 mg, 1.42 mmol, 0.200 mL) in dry MeCN (10.0 mL). The product is purified by reverse phase HPLC: Gilson prep pumps; Flow rate: 30 ml/min; Column: Gemini (50 21.2×50 mm; Mobile phase: A=10.0 mM NH4HCO3 in H2O B=MeCN (52.4 mg, 0.129 mmol, 27.0%). 1H NMR (400 MHz, DMSO-D6) δ ppm 1.36 (d, J=7.03 Hz, 3H) 1.70 (s, 6H) 2.40 (s, 3H) 4.72-4.90 (m, 1H) 5.17 (dd, J=21.48, 17.19 Hz, 2H) 7.18 (d, J=7.81 Hz, 1H) 7.21-7.32 (m, 2H) 7.40 (t, J=8.30 Hz, 1H) 7.72 (d, J=7.62 Hz, 1H) 7.86 (d, J=7.81 Hz, 1H) 8.22 (s, 1H) 8.72 (d, J=7.42 Hz, 1H); MS [M+H] calcd.: 407.18. found: 407.17.

Workup

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

Sources & evidence

ORD record
ord-ce303c8e96324171ae7b63961a46efda
Source dataset
uspto-grants-2012_01
Patent number
US08093402B2

Reaction notes

Loading…