Ammonium Chloride → HCID 178421936, compound

HRID 731078Notes

Reaction equation

HRID 731078 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([C:17]3[CH:26]=[CH:25][C:20]([O:21][CH2:22][C:23]#[N:24])=[CH:19][CH:18]=3)[CH:13]=[CH:14][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](=[C:12]([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:13]=[CH:14][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 68814808HCID 68814808, compound

Product 1

HCID 178421936HCID 178421936, 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-4-yl)-phenoxy]-acetonitrile (0.270 g, 0.630 mmol) was reacted with NaN3 (0.205 g, 3.150 mmol) and NH4Cl (0.168 g, 3.150 mmol) in DMF (5 ml) to give the product (0.211 g, 0.447 mmol, 71%) as a white solid, mp 174-177° C. 1H NMR (DMSO-d6) δ 1.71 (s, 3H), 5.30 (s, 2H), 5.52 (s, 2H), 6.84 (d, J=7.0 Hz, 1H), 6.88 (d, J=7.0 Hz, 2H), 7.10-7.13 (m, 3H), 7.16 (t, J=7.0 Hz, 1H), 7.22 (t, J=7.0 Hz, 2H), 7.32-7.35 (m, 3H), 7.37-7.47 (m, 5H); IR (solid) 3020, 2910, 2860, 1605, 1510, 1480, 1440 and 1230 cm−1; [ESI(−)], m/z 470 (M−H)−; Anal. Calcd. for C30H25N5O: C, 76.41; H, 5.34; N, 14.85; Found: C, 76.42; H, 5.21; N, 14.95.

Sources & evidence

ORD record
ord-21680f0d215f4e4686d30bdc3cbd180a
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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