Ammonium Chloride → HCID 178446888, compound

HRID 1359243Notes

Reaction equation

HRID 1359243 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[O:13][C:14]4[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:15]=4[C:16]=3[C:17](=[O:22])[CH2:18][CH2:19][CH2:20][CH3:21])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:28][CH2:29][C:30]#[N:31].[N-:32]=[N+:33]=[N-:34].[Na+].[Cl-].[NH4+]>CN(C=O)C>[Br:1][C:2]1[C:3]([O:28][CH2:29][C:30]2[NH:34][N:33]=[N:32][N:31]=2)=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[CH:9][C:8]([C:12]1[O:13][C:14]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:15]=3[C:16]=1[C:17](=[O:22])[CH2:18][CH2:19][CH2:20][CH3:21])=[CH:7]2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 18182774HCID 18182774, compound

Product 1

HCID 178446888HCID 178446888, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the procedure described in Step 6, of Example 1, the title compound was prepared from [1-bromo-6-(5-chloro-3-pentanoyl-benzofuran-2-yl)-naphthalen-2-yloxy]-acetonitrile (0.4 g, 0.8 mmol), sodium azide (0.325 g, 5 mmol) and ammonium chloride (0.268 g, 5 mmol) in DMF (20 mL). The compound was purified by flash chromatography on acid treated silica gel using 50% ethyl acetate in hexane as the mobile phase. The title compound was obtained as an off-white solid (0.32 g), mp 133-135° C. Mass spectrum (−ESI, [M−H]−) m/z 537. 1HNMR (400 MHz, DMSO-d6): δ8.51 (d, 1H, J=1.5 Hz), 8.26-8.20 (m, 2H), 8.03-7.99 (m, 2H), 7.80-7.76 (m, 2H), 7.48 (dd, 1H, J=8.8, 2.2 Hz), 5.78 (s, 2H), 2.73 (t, 2H, J=7.3 Hz), 1.56-1.49 (m, 2H), 1.17-1.08 (m, 2H), and 0.70 ppm (t, 3H, J=7.3 Hz). Elemental Analysis for C25H20BrClN4O3: Calculated: C, 55.63; H, 3.73; N, 10.38. Found: C, 55.54; H, 3.59; N, 10.24.

Workup

  1. customThe compound was purified by flash chromatography on acid
  2. additiontreated silica gel using 50% ethyl acetate in hexane as the mobile phase

Sources & evidence

ORD record
ord-0214f6e87265413aad55801bad06d6b5
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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