Ammonium Chloride → HCID 178422617, compound

HRID 731057Notes

Reaction equation

HRID 731057 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[CH3:34])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:35]=[N+:36]=[N-:37].[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:37][N:36]=[N:35][N:24]=4)=[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[CH3:34])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 68814248[4-(1,3-Dibenzyl-2-methyl-1H-indol-5-yl)-phenoxy]-acetonitrile

Product 1

HCID 178422617HCID 178422617, 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-methyl-1H-indol-5-yl)-phenoxy]-acetonitrile (0.160 g, 0.362 mmol) was reacted with NaN3 (0.118 g, 1.808 mmol) and NH4Cl (0.097 g, 1.808 mmol) in DMF (5 ml) to give the product (0.136 g, 0.280 mmol, 77%) as a white solid, mp 190-192° C. 1H NMR (DMSO-d6) δ 2.35 (s, 3H), 4.10 (s, 2H), 5.43 (s, 2H), 5.49 (s, 2H), 6.99 (d, J=7.0 Hz, 2H), 7.09-7.13 (m, 3H), 7.20-7.30 (m, 8H), 7.40 (d, J=8.4 Hz, 1H), 7.54 (d, J=8.9 Hz, 2H), 7.60 (d, J=1.7 Hz, 1H); IR (solid) 3030, 2905, 2850, 1605, 1520, 1480, 1440, 1360, 1270, and 1250 cm−1; [ESI(−)], m/z 484 (M−H)−; Anal. Calcd. for C31H27N5O: C, 76.88; H, 5.60; N, 14.42; Found: C, 76.71; H, 5.57; N, 14.37.

Sources & evidence

ORD record
ord-dfe9264dfe8e46c794c0e67ab5924326
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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