Ammonium Chloride → HCID 178446886, compound

HRID 1359210Notes

Reaction equation

HRID 1359210 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][CH:24]=[CH:23][C:15]=4[C:16]=3[C:17](=[O:22])[CH2:18][CH:19]([CH3:21])[CH3:20])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:27][CH2:28][C:29]#[N:30].[N-:31]=[N+:32]=[N-:33].[Na+].[Cl-].[NH4+]>CN(C=O)C>[Br:1][C:2]1[C:3]([O:27][CH2:28][C:29]2[NH:33][N:32]=[N:31][N:30]=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][CH:24]=[CH:23][C:15]=3[C:16]=1[C:17](=[O:22])[CH2:18][CH:19]([CH3:21])[CH3:20])=[CH:7]2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 18182794HCID 18182794, compound

Product 1

HCID 178446886HCID 178446886, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the procedure described in Step 6, of Example 1, the title compound was prepared from 2-({1-bromo-6-[3-(3-methylbutanoyl)-1-benzofuran-2-yl]-2-naphthyl}oxy) acetonitrile (0.207 g, 0.448 mmol), sodium azide (0.147 g, 2.26 mmol) and ammonium chloride (0.125 g, 2.34 mmol) in DMF (10 mL). The compound was purified by HPLC using 75% acetonitrile/0.1% TFA in water. Drying for 14 hours at 90° C. yielded a cream-colored solid (0.0966 g), mp 176-177° C. Mass spectrum (−ESI, [M−H]−) m/z 503. 1HNMR (500 MHz, DMSO-d6): δ16.8-17.1 (br s, 1H), 8.5 (d, 1H, J=1.7 Hz), 8.25 (q, 2H, J=8.2 Hz), 8.0-8.05 (m, 2H), 7.75 (q, 2H, J=8.3 Hz), 7.4-7.5 (m, 3H), 5.8 (s, 2H), 2.7 (d, 2H, J=6.9 Hz), 2.05-2.15 (m, 1H), and 0.75 ppm (d, 6H, J=6.6 Hz). Elemental Analysis for C25H21BrN4O3.0.10 H2O: Calculated: C, 59.20; H, 4.21; N, 11.05. Found: C, 58.84; H, 3.80; N, 10.83.

Workup

  1. customThe compound was purified by HPLC
  2. customDrying for 14 hours at 90° C.

Sources & evidence

ORD record
ord-81aea37f6e764be4ba4d5482cb00d9d5
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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