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

HRID 419984Notes

Reaction equation

HRID 419984 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([CH2:10][C:11]([OH:13])=O)[C:6]=2[C:14]=1[F:15].[NH2:16][CH:17]([C:19]1[CH:24]=[CH:23][C:22]([C:25]2([C:31]#[N:32])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:21][CH:20]=1)[CH3:18].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:31]([C:25]1([C:22]2[CH:21]=[CH:20][C:19]([CH:17]([NH:16][C:11](=[O:13])[CH2:10][N:7]3[C:6]4[C:14]([F:15])=[C:2]([F:1])[CH:3]=[CH:4][C:5]=4[N:9]=[CH:8]3)[CH3:18])=[CH:24][CH:23]=2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)#[N:32]

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 57939018HCID 57939018, compoundHCID 582984371-[4-(1-Aminoethyl)phenyl]cyclohexanecarbonitrile

Product 1

HCID 24850119N-{1-[4-(1-Cyanocyclohexyl)phenyl]ethyl}-2-(6,7-difluoro-1H-benzimidazol-1-yl)acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

N-{1-[4-(1-Cyanocyclohexyl)phenyl]ethyl}-2-(6,7-difluoro-1H-benzimidazol-1-yl)acetamide is synthesized according to example 5 by mixing (6,7-difluoro-1H-benzimidazol-1-yl)acetic acid (233 mg, 1.10 mmol) prepared according to scheme 2, 1-[4-(1-aminoethyl)phenyl]cyclohexanecarbonitrile (250 mg, 1.10 mmol) prepared according to scheme 11, Et3N (111 mg, 1.10 mmol, 0.153 mL) and HATU (418 mg, 1.10 mmol) in MeCN (10.0 mL). The product is purified by HPLC: Gilson prep pumps, Flow rate: 30 ml/min, Column: Gemini (5μ) 21.2×50 mm, Mobile phase: A=water (10 mM NH4CO3) B=MeCN, (336 mg, 0.796 mmol, 72%). 1H NMR (400 MHz, DMSO-D6) δ ppm 1.38 (d, J=7.03 Hz, 3H) 1.23-1.35 (m, 1H) 1.51-1.69 (m, 2H) 1.69-1.78 (m, 1H) 1.77-1.89 (m, 4H) 1.99-2.09 (m, 2H) 4.87-5.00 (m, 1H) 5.07 (s, 2H) 7.14-7.28 (m, 1H) 7.37 (d, J=8.40 Hz, 2H) 7.42-7.53 (m, 3H) 8.19 (s, 1H) 8.83 (d, J=7.81 Hz, 1H); MS [M+H], calcd: 424.0. found: 423.3.

Workup

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

Sources & evidence

ORD record
ord-e4a63bd1d0814f9a99b336c0b74a3af6
Source dataset
uspto-grants-2012_01
Patent number
US08093402B2

Reaction notes

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