3-(Prop-2-ynyloxy)pyridine → HCID 44273429, compound

HRID 1032763Notes

Reaction equation

HRID 1032763 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16](I)[S:17][C:13]=2[N:12]2[C:19]([CH3:22])=[N:20][N:21]=[C:11]2[CH2:10][N:9]=1.[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH2:30][C:31]#[CH:32])[CH:24]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([C:32]#[C:31][CH2:30][O:29][C:25]3[CH:24]=[N:23][CH:28]=[CH:27][CH:26]=3)[S:17][C:13]=2[N:12]2[C:19]([CH3:22])=[N:20][N:21]=[C:11]2[CH2:10][N:9]=1

Participants

3

Reactant 2

HCID 114236223-(Prop-2-ynyloxy)pyridineHCID 148519244-(2-chlorophenyl)-2-iodo-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine

Product 1

HCID 44273429HCID 44273429, compound

Procedure

Coupling of 4-(2-chlorophenyl)-2-iodo-9-methyl -6H-thieno[3,2-f][1,2,4] triazolo[4,3-a][1,4]diazepine with 1-(3-pyridinyloxy)-2-propyne [ref. J. Bruhn J., Zsindely, H. Schmid and G. Frater, Helv. Chim. Acta 61, 2542 (1978)] under conditions described in EXAMPLE 37 yielded after the usual chromatographic isolation resinous material containing the title compound which did not crystallize and was therefore characterized spectroscopically only. Nmr (CDCl3): 2.72 ppm (s,3,Me) 4.95 (s,4,CH2 ; C6 -H), 6.8 (s.1,C3 -H) 7.2-7.6 (m,6,aromatic H), 8.26 (m,1,) and 8.36 (broad s,1) pyridine C2 and C6 -H).

Workup

  1. customyielded after the usual chromatographic isolation resinous material

Sources & evidence

ORD record
ord-5012b95669eb4af1bb5d55c6a9a3c7f0
Source dataset
uspto-grants-1990_09
Patent number
US04959361

Reaction notes

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