Ammonium Chloride → HCID 178421935, compound

HRID 731071Notes

Reaction equation

HRID 731071 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]3[CH:26]=[CH:25][C:20]([O:21][CH2:22][C:23]#[N:24])=[CH:19][CH:18]=3)[CH:15]=2)[C:10]([CH3:27])=[C:9]1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:34]=[N+:35]=[N-:36].[Na+].[NH4+].[Cl-]>CN(C=O)C>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]3[CH:26]=[CH:25][C:20]([O:21][CH2:22][C:23]4[NH:36][N:35]=[N:34][N:24]=4)=[CH:19][CH:18]=3)[CH:15]=2)[C:10]([CH3:27])=[C:9]1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 68813999HCID 68813999, compound

Product 1

HCID 178421935HCID 178421935, 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-methyl-2-phenyl-1H-indol-6-yl)-phenoxy]-acetonitrile (0.288 g, 0.672 mmol) was reacted with NaN3 (0.218 g, 3.360 mmol) and NH4Cl (0.180 g, 3.360 mmol) in DMF (5 ml) to give the product (0.245 g, 0.520 mmol, 77%) as a white solid, dec. 224.5-226° C. 1H NMR (DMSO-d6) δ 2.23 (s, 3H), 5.39 (s, 2H), 5.50 (s, 2H), 6.85 (d, J=7.3 Hz, 2H), 7.12 (t, J=8.4 Hz, 3H), 7.18 (t, J=7.0 Hz, 2H), 7.35-7.44 (m, 4H), 7.48 (t, J=7.2 Hz, 2H), 7.60-7.62 (m, 4H), 16.80 (broad s, 1H); IR (solid) 3020, 2910, 1605, 1520, 1480, 1460, 1340 and 1240 cm−1; [ESI(−)], m/z 470 (M−H)−; Anal. Calcd. for C30H25N5O: C, 76.41; H, 5.34; N, 14.85; Found: C, 76.33; H, 5.28; N, 14.91.

Sources & evidence

ORD record
ord-0425a7ccd68341f09f8ff785e4b9fe97
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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