Isopropanol → HCID 178420752, compound

HRID 1170497Notes

Reaction equation

HRID 1170497 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][NH:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:26][C:27]#[N:28])[C:16]3[S:20][N:19]=[C:18]([N:21]4[CH:25]=[CH:24][N:23]=[CH:22]4)[N:17]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.[N-:29]=[N+:30]=[N-:31].[Na+].CC(O)C.C(Cl)Cl>[Br-].[Zn+2].[Br-].C(Cl)Cl.CO>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][NH:11][CH2:12][CH2:13][CH2:14][N:15]([C:16]3[S:20][N:19]=[C:18]([N:21]4[CH:25]=[CH:24][N:23]=[CH:22]4)[N:17]=3)[CH2:26][C:27]3[NH:31][N:30]=[N:29][N:28]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 6344DichloromethaneHCID 33557Sodium AzideHCID 11625423HCID 11625423, compound

Product 1

HCID 178420752HCID 178420752, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of [{3-[(benzo[1,3]dioxol-5-ylmethyl)-amino]-propyl}-(3-imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-amino]-acetonitrile (37 mg, 91 μmol), sodium azide (12 mg, 184 μmol) and zinc (II) bromide (10 mg, 46 μmol) in 2:1H2O/iPrOH (1 mL) was heated to 150° C. for 24 h. The reaction mixture was cooled to r.t. prior to loading directly onto a SiO2 column (CH2Cl2 to 4:1 CH2Cl2/MeOH) to afford 14 mg (35%) of N′-benzo[1,3]dioxol-5-ylmethyl-N-(3-imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-N-(1H-tetrazol-5-ylmethyl)-propane-1,3-diamine as a white solid. [M+H]+ 441.01; 1H NMR (400 MHz, CD3OD) δ 8.35 (s, 1H), 7.74 (s, 1H), 7.07 (s, 1H), 6.85-6.74 (m, 3H), 5.92 (s, 2H), 4.43 (s, 2H), 4.06 (s, 2H), 3.81 (br s, 2H), 3.31 (t, 2H), 3.06 (t, 2H), 2.17 (tt, 2H).

Sources & evidence

ORD record
ord-093fdc5eec324c678c6379f68ddc39e9
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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