Triethylamine → 2-(3,5-bis-(4-Fluoro-phenyl)-(1,2,4)triazol-1-yl]-1-(4,5,7,8-tetrahydro-thiazolo[4,5-d]azepin-6-yl)-ethanone

HRID 239195Notes

Reaction equation

HRID 239195 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[N:10]([CH2:20][C:21]([OH:23])=O)[N:9]=2)=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[S:55]1[C:64]2[CH2:63][CH2:62][NH:61][CH2:60][CH2:59][C:58]=2[N:57]=[CH:56]1>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[N:10]([CH2:20][C:21]([N:61]3[CH2:62][CH2:63][C:64]4[S:55][CH:56]=[N:57][C:58]=4[CH2:59][CH2:60]3)=[O:23])[N:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 226207475,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepineHCID 86686517(3,5-bis-(4-Fluoro-phenyl)-(1,2,4)triazol-1-yl)-acetic acid

Product 1

HCID 866865262-(3,5-bis-(4-Fluoro-phenyl)-(1,2,4)triazol-1-yl]-1-(4,5,7,8-tetrahydro-thiazolo[4,5-d]azepin-6-yl)-ethanoneYield 52.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

32 mg (3,5-bis-(4-fluoro-phenyl)-(1,2,4)triazol-1-yl)-acetic acid was dissolved in 1.5 mL DMF. 32 mg HATU and 15 μL triethylamine were added to this solution and the mixture was stirred for 5 min. at RT. Then, 15 mg 5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepine and 15 μL triethylamine in 0.5 mL DMF were added. The mixture was stirred over night at RT. The reaction solution was purified by HPLC to yield 23 mg of the desired compound.

Workup

  1. stirringThe mixture was stirred over night at RT
  2. customThe reaction solution was purified by HPLC

Sources & evidence

ORD record
ord-cccc04aefb904ff68999af71984b4f8a
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

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