Nitrogen → HCID 86653116, compound

HRID 1258560Notes

Reaction equation

HRID 1258560 reaction equation
Cl[C:2]1[S:3][C:4]([Cl:23])=[C:5]([CH2:7][O:8][N:9]=[C:10]([C:17]2[N:21]([CH3:22])[N:20]=[N:19][N:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:6]=1.N#N.[CH:26]1([C:29]#[CH:30])[CH2:28][CH2:27]1.C(N(C(C)C)C(C)C)C>C1COCC1.CCOC(C)=O.[Cu](I)I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:23][C:4]1[S:3][C:2]([C:30]#[C:29][CH:26]2[CH2:28][CH2:27]2)=[N:6][C:5]=1[CH2:7][O:8][N:9]=[C:10]([C:17]1[N:21]([CH3:22])[N:20]=[N:19][N:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

9

Reactant 4

HCID 947NitrogenHCID 81531DiisopropylethylamineHCID 138823CyclopropylacetyleneHCID 86653109HCID 86653109, compound

Product 1

HCID 86653116HCID 86653116, compoundYield 84.6%

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of N-[(2,5-dichloro-1,3-thiazol-4-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (0.15 g, 0.406 mmol, 1 eq.) in 3 ml dry THF “degassed” with N2, was added Cyclopropylacetylene (0.029 g, 0.447 mmol, 1.1 eq.) followed by N-ethyldiisopropylamine (0.209 g, 1.62 mmol, 4 eq.), Copper Iodide (0.015 g, 0.081 mmol, 0.2 eq.) and Tetrakis(triphenylphosphine)palladium (0.046 g, 0.041 mmol, 0.1 eq.). The reaction was microwaved 120° C./normal/fixed hold/pre stir 100 s for 180 s. The reaction was diluted with EtOAc and filtered through a “celite” plug. The solvent was evaporated and the residue purified by chromatography on silica gel to give N-{[5-chloro-2-(cyclopropylethynyl)-1,3-thiazol-4-yl]methoxy}-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (0.137 g, 71% yield, 78:5 mixture of stereoisomers) as a yellow viscous oil.

Workup

  1. customThe reaction was microwaved 120° C./normal/fixed hold/pre
  2. filtrationfiltered through a “celite” plug
  3. customThe solvent was evaporated
  4. customthe residue purified by chromatography on silica gel

Sources & evidence

ORD record
ord-c47d7eae18074afdbc7cc9a09684770c
Source dataset
uspto-grants-2013_06
Patent number
US08466176B2

Reaction notes

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