Triethylamine hydrochloride → HCID 59599530, compound

HRID 2267000Notes

Reaction equation

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

Participants

Reactant 3

HCID 11130Triethylamine hydrochloride

HCID 33557Sodium Azide

HCID 68535727HCID 68535727, compound

Product 1

HCID 59599530HCID 59599530, compoundYield 48%

Procedure

Using the procedure essentially as described for Example 1 using 2-[3-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenylsulfanyl]-nicotinonitrile (350 mg, 0.836 mmol), sodium azide (544 mg, 8.36 mmol), and triethylamine hydrochloride (1.15 g, 8.36 mmol) to yield the title compound as a tan solid (185 mg, 48%): 1H NMR (DMSO-d6) δ 0.796 (t, 3H), 1.45 (sextuplet, 2H), 2.56 (t, 2H), 2.58 (s, 3H), 5.29 (s, 2H), 6.73 (d, 1H), 7.38 (dd, 1H), 7.48 (m, 3H), 7.57 (s, 1H), 7.82 (d, 1H), 8.16 (d, 1H), 8.44 (dd, 1H), 12.84 (s, 1H); MS (esi negative) m/z 460 (m−1).

Sources & evidence

ORD record: ord-e47ffca4945f4c6594b08979a9b1ff69
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858646B2

Reaction notes

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