6-(4-{[4-(2-oxo-2,3-Dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-5-phenylnicotinonitrile → HCID 178518592, compound

HRID 2105510Notes

Reaction equation

HRID 2105510 reaction equation
[O:1]=[C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[C:27]([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)=[CH:26][C:23]([C:24]#[N:25])=[CH:22][N:21]=4)=[CH:16][CH:15]=3)[CH2:9][CH2:8]2)[C:5]2[CH:34]=[CH:35][CH:36]=[CH:37][C:4]=2[NH:3]1.[N-:38]=[N+:39]=[N-:40].[Na+].O>[Zn+2].[Br-].[Br-].O>[C:28]1([C:27]2[C:20]([C:17]3[CH:16]=[CH:15][C:14]([CH2:13][N:10]4[CH2:9][CH2:8][CH:7]([N:6]5[C:5]6[CH:34]=[CH:35][CH:36]=[CH:37][C:4]=6[NH:3][C:2]5=[O:1])[CH2:12][CH2:11]4)=[CH:19][CH:18]=3)=[N:21][CH:22]=[C:23]([C:24]3[NH:40][N:39]=[N:38][N:25]=3)[CH:26]=2)[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 99570316-(4-{[4-(2-oxo-2,3-Dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-5-phenylnicotinonitrileHCID 86609354Water sodium azide

Product 1

HCID 178518592HCID 178518592, compound

Reagents, catalysts & solvents 1

HCID 86609355ZnBr2 waterCatalyst

Procedure

A mixture of 6-(4-{[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-5-phenylnicotinonitrile (1-5; TFA salt) (71 mg, 0.1 mmol), 2M of NaN3 water solution (0.75 mL, 1.5 mmol), 2M of ZnBr2 water solution (0.5 mL, 1.0 mmol) was microwaved (Smith-Synthesizer) at 165° C. for 15 min. After this time, the solution was concentrated. The residue was re-dissolved in DMSO (1 mL) and purified by LCMS to afford the pure desired product (1-6; TFA salt) as a slightly yellow solid. Analytical LCMS: single peak (214 nm), 2.248 min. 1H NMR (500 MHz, DMSO-d6): δ 10.94 (s, 1H), 9.74-9.90 (s, 1H), 9.33 (d, J=2.1 Hz, 1H), 8.44 (d, J=2.1 Hz, 1H), 7.47-7.50 (s, 4H), 7.36-7.40 (m, 3H), 7.26-7.30 (m, 3H), 6.98-7.02 m, 3H), 4.45-4.54 (m, 1H), 4.33-4.38 (s, 2H), 3.49 (d, J=12.7 Hz, 2H), 3.13-3.23 (m, 2H), 2.58-2.69 (m, 2H), 1.95 (d, J=12.8 Hz, 2H); HRMS, calc'd for C31H29N8O (M+1), 529.2459; found 529.2449.

Workup

  1. customwas microwaved (Smith-Synthesizer) at 165° C. for 15 min
  2. concentrationAfter this time, the solution was concentrated
  3. dissolutionThe residue was re-dissolved in DMSO (1 mL)
  4. custompurified by LCMS

Sources & evidence

ORD record
ord-e4992dd8ca2e45989c1c74002c3439d0
Source dataset
uspto-grants-2009_08
Patent number
US07579355B2

Reaction notes

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