Ammonium Chloride → HCID 178442050, compound

HRID 731092Notes

Reaction equation

HRID 731092 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:26]=[CH:25][C:20]([O:21][CH2:22][C:23]#[N:24])=[CH:19][CH:18]=3)=[CH:14][CH:15]=2)[C:10]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[C:9]1[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:38]=[N+:39]=[N-:40].[Na+].[NH4+].[Cl-]>CN(C=O)C>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:26]=[CH:25][C:20]([O:21][CH2:22][C:23]4[NH:40][N:39]=[N:38][N:24]=4)=[CH:19][CH:18]=3)=[CH:14][CH:15]=2)[C:10]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[C:9]1[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 68813877[4-(1-Benzyl-3-pentyl-2-phenyl-1H-indol-5-yl)-phenoxy]-acetonitrile

Product 1

HCID 178442050HCID 178442050, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The desired product was prepared using a procedure similar to step 6 of example 3. Thus, [4-(1-benzyl-3-pentyl-2-phenyl-1H-indol-5-yl)-phenoxy]-acetonitrile (0.252 g, 0.520 mmol) was reacted with NaN3 (0.169 g, 2.6 mmol) and NH4Cl (0.139 g, 2.6 mmol) in DMF (5 ml) to give the product (0.137 g, 0.260 mmol, 50%) as a white solid, mp 165-168° C. 1H NMR (DMSO-d6) δ 0.76 (t, J=7.0 Hz, 3H), 1.15-1.22 (m, 4H), 1.53-1.59 (m, 2H), 2.68 (t, J=7.5 Hz, 2H), 5.27 (s, 2H), 5.52 (s, 2H), 6.83 (d, J=7.2 Hz, 2H), 7.13-7.16 (m, 3H), 7.20 (t, J=6.9 Hz, 2H), 7.34-7.38 (m, 4H), 7.43 (t, J=7.0 Hz, 1H), 7.48 (t, J=6.9 Hz, 2H), 7.63 (d, J=8.6 Hz, 2H), 7.77 (S; 1H), 16.79 (broad s, 1H); IR (solid) 3030, 2920, 2850, 1605, 1520, 1480, 1260 and 1240 cm−1; [ESI(−)], m/z 527 (M−H)−; Anal. Calcd. for C34H33N5O: C, 77.39; H, 6.30; N, 13.27; Found: C, 77.34; H, 6.33; N, 13.30.

Sources & evidence

ORD record
ord-15a6224730e14420b3db6b0cfc94f658
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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