Triethylamine hydrochloride → HCID 57884489, compound

HRID 1161124Notes

Reaction equation

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

Participants

Reactant 3

HCID 11130Triethylamine hydrochloride

HCID 33557Sodium Azide

HCID 66699620HCID 66699620, compound

Product 1

HCID 57884489HCID 57884489, compoundYield 68.4%

Procedure

Using the general procedure of Example 1 using 5-[4-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-benzoyl]-nicotinonitrile (448 mg, 1.08 mmol), sodium azide (703 mg, 10.8 mmol), and triethylamine hydrochloride (1.49 g, 10.8 mmol) to yield the title product as a white solid (338 mg, 66%): 1H NMR (DMSO-d6) δ 0.90 (t, 3H), 1.53 (sextet, 2H), 2.59 (s, 3H), 2.64 (t, 2H), 5.43 (s, 2H), 6.76 (d, 1H), 7.67 (d, 2H), 7.84 (d, 1H), 7.92 (d, 2H), 8.68 (t, 1H), 9.05 (d, 1H), 9.46 (d, 1H), 12.86 (s, 1H); MS (esi negative) m/z (rel intensity) 456 (100).

Sources & evidence

ORD record: ord-576cfd580c064901a4f14473b666ac5f
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816523B2

Reaction notes

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