Ammonium Chloride → HCID 178420190, compound

HRID 731106Notes

Reaction equation

HRID 731106 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][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:9]1[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:40]=[N+:41]=[N-:42].[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:42][N:41]=[N:40][N:24]=4)=[CH:19][CH:18]=3)=[CH:14][CH:15]=2)[C:10]([CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[C:9]1[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 68814513HCID 68814513, compound

Product 1

HCID 178420190HCID 178420190, 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-(1,3-dibenzyl-2-phenyl-1H-indol-5-yl)-phenoxy]-acetonitrile (0.481 g, 0.953 mmol) was reacted with NaN3 (0.310 g, 4.766 mmol) and NH4Cl (0.255 g, 4.766 mmol) in DMF (5 ml) to give the product (0.394 g, 0.719 mmol, 75%) as an off-white solid, dec. 191-194° C. 1H NMR (DMSO-d6) δ 4.08 (s, 2H), 5.35 (s, 2H), 5.51 (s, 2H), 6.89 (d, J=7.2 Hz, 2H), 7.10-7.25 (m, 10H), 7.37 (dd, J=1.7 Hz, 8.5 Hz, 1H), 7.40-7.54 (m, 8H), 7.61 (s, 1H), 16.80 (broad s, 1H); IR (solid) 3020, 2920, 1605, 1520, 1470, 1450, 1360, and 1240 cm−1; [ESI(−)], m/z 546 (M−H)−; Anal. Calcd. for C36H29N5O: C, 78.95; H, 5.34; N, 12.79; Found: C, 78.53H, 5.25; N, 12.77.

Sources & evidence

ORD record
ord-70fd958006ce477a93b83bffbb320993
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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