Ammonium Chloride → HCID 178442049, compound

HRID 731099Notes

Reaction equation

HRID 731099 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[CH:20]=[CH:19][C:14]([O:15][CH2:16][C:17]#[N:18])=[CH:13][CH:12]=3)=[CH:8][CH:9]=2)[C:4]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[C:3]1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[N-:32]=[N+:33]=[N-:34].[Na+].[NH4+].[Cl-]>CN(C=O)C>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[CH:20]=[CH:19][C:14]([O:15][CH2:16][C:17]4[NH:34][N:33]=[N:32][N:18]=4)=[CH:13][CH:12]=3)=[CH:8][CH:9]=2)[C:4]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[C:3]1[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 68815874HCID 68815874, compound

Product 1

HCID 178442049HCID 178442049, 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-methyl-3-pentyl-2-phenyl-1H-indol-5-yl)-phenoxy]-acetonitrile (0.152 g, 0.372 mmol) was reacted with NaN3 (0.121 g, 1.860 mmol) and NH4Cl (0.099 g, 1.860 mmol) in DMF (5 ml) to give the product (0.117 g, 0.259 mmol, 70%) as a white solid, dec. 181-185° C. 1H NMR (DMSO-d6) δ 0.76 (t, J=7.0 Hz, 3H), 1.13-1.22 (m, 4H), 1.51-1.57 (m, 2H), 2.66 (t, J=7.5 Hz, 2H), 3.56 (s, 3H), 5.53 (s, 2H), 7.15 (d, J=8.7 Hz, 2H), 7.42-7.45 (m, 3H), 7.48 (t, J=8.6 Hz, 2H), 7.54 (t, J=7.2 Hz, 2H), 7.65 (d, J=8.7 Hz, 2H), 7.74 (d, J=1.2 Hz, 1H), 16.80 (broad s, 1H); IR (solid) 3030, 2930, 2860, 1605, 1520, 1480, 1370 and 1240 cm−1; [ESI(−)], m/z 450 (M−H)−; Anal. Calcd. for C28H29N5O: C, 74.48; H, 6.47; N, 15.51 Found: C, 74.49; H, 6.26; N, 15.30.

Sources & evidence

ORD record
ord-ca0ef816c02342f5bd0f0be4c5fb3746
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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