Dimethylformamide → HCID 178438900, compound

HRID 1162576Notes

Reaction equation

HRID 1162576 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([N:15]([CH2:20][C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)[CH2:16][CH2:17][C:18]#[N:19])[S:13][CH:14]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[N-:26]=[N+:27]=[N-:28].[Na+].[Cl-].[NH4+].CN(C=O)C>C(O)(=O)C>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[C:12]([N:15]([CH2:16][CH2:17][C:18]3[NH:28][N:27]=[N:26][N:19]=3)[CH2:20][C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)[S:13][CH:14]=2)=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 68648406HCID 68648406, compound

Product 1

HCID 178438900HCID 178438900, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

[4-(4-Isopropyl-phenyl)-thiazol-2-yl]-[2-(1H-tetrazol-5-yl)-ethyl]-thiophen-2-ylmethyl-amine was prepared following general procedure H using 3-{[4-(4-isopropyl-phenyl)-thiazol-2-yl]-thiophen-2-ylmethyl-amino}-propionitrile (278 mg, 0.756 mmol), sodium azide (657 mg, 99%, 10 mmol), ammonium chloride (535 mg, 10 mmol) and DMF (3 mL). Purification by flash chromatography (ethyl acetate/hexanes 1:1, with 0.5% v/v acetic acid) gave the product compound (110 g, 0.268 mmol).

Workup

  1. customPurification by flash chromatography (ethyl acetate/hexanes 1:1

Sources & evidence

ORD record
ord-d04fdd47ce984abba530b5effd2ea333
Source dataset
uspto-grants-2010_10
Patent number
US07820704B2

Reaction notes

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