Ammonium Chloride → HCID 178479922, compound

HRID 731113Notes

Reaction equation

HRID 731113 reaction equation
[CH2:1]([C: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)[N: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]([C: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)[N: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 68814796HCID 68814796, compound

Product 1

HCID 178479922HCID 178479922, 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-(3-benzyl-1-methyl-2-phenyl-1H-indol-5-yl)-phenoxy]-acetonitrile (0.137 g, 0.320 mmol) was reacted with NaN3 (0.104 g, 1.598 mmol) and NH4Cl (0.085 g, 1.598 mmol) in DMF (5 ml) to give the product (0.102 g, 0.216 mmol, 68%) as a pale-yellow solid, dec. 194-197° C. 1H NMR (DMSO-d6) δ 3.59 (s, 3H), 4.01 (s, 2H), 5.46 (s, 2H), 7.03-7.09 (m, 5H), 7.13-7.17 (m, 2H), 7.39-7.53 (m, 9H), 7.55 (d, J=1.2 Hz, 1H), 16.75 (broad s, 1H); IR (solid) 3020, 2920, 1605, 1520, 1480, 1450, 1370 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, 76.35; H, 5.28; N, 14.90.

Sources & evidence

ORD record
ord-1c8acf8bd01a4f90a70792fbadcbd03f
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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