Methanol → HCID 178446892, compound

HRID 1359245Notes

Reaction equation

HRID 1359245 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:11]=[C:12]4[C:17](=[CH:18][CH:19]=3)[CH:16]=[C:15]([O:20][CH2:21][C:22]#[N:23])[CH:14]=[CH:13]4)=[C:7]([C:24](=[O:29])[CH2:25][CH2:26][CH2:27][CH3:28])[C:6]=2[CH:30]=1.[N-:31]=[N+:32]=[N-:33].[Na+].[Cl-].[NH4+].CO>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:19]=[CH:18][C:17]4[C:12](=[CH:13][CH:14]=[C:15]([O:20][CH2:21][C:22]5[NH:33][N:32]=[N:31][N:23]=5)[CH:16]=4)[CH:11]=3)=[C:7]([C:24](=[O:29])[CH2:25][CH2:26][CH2:27][CH3:28])[C:6]=2[CH:30]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 18182819HCID 18182819, compound

Product 1

HCID 178446892HCID 178446892, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the procedure described in Step 6, of Example 1, the title compound was prepared from [6-(5-Chloro-3-pentanoyl-benzofuran-2-yl)-naphthalen-2-yloxy]-acetonitrile (0.31 g, 0.74 mmol), sodium azide (0.325 g, 5 mmol) and ammonium chloride (0.268 g, 5 mmol) in DMF (20 mL). Trituration with methanol afforded the title compound as a yellow solid (0.26 g), mp 178-180° C. Mass spectrum (+APCl, [M+H]+) m/z 461. 1HNMR (400 MHz, DMSO-d6): δ8.4 (s, 1H), 8.07-7.99 (m, 3H), 7.85 (dd, 1H, J=8.5, 1.7 Hz), 7.77 (d, 1H, J=8.8 Hz),), 7.64 (d, 1H, J=2.2 Hz),), 7.48 (dd, 1H, J=8.8, 2.2 Hz),), 7.38 (dd, 1H, J=8.8, 2.4 Hz), 5.66 (s, 2H), 2.70 (t, 2H, J=7.4 Hz), 1.56-1.48 (m, 2H), 1.15-1.06 (m, 2H), and 0.69 ppm (t, 3H, J=7.5 Hz). Elemental Analysis for C25H21ClN4O3.0.5H2O: Calculated: C, 64.52; H, 4.66; N, 12.04. Found: C, 64.40; H, 4.42; N, 12.07.

Sources & evidence

ORD record
ord-7d4883a2a4c348ba92dcadbf8948bc0a
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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