Diisopropylethylamine → 1-(2-Bromo-4,5,7,8-tetrahydro-thiazolo[4,5-d]azepin-6-yl)-2-(5-(4-fluoro-phenyl)-3-p-tolyl-(1,2,4)triazol-1-yl)-ethanone

HRID 239188Notes

Reaction equation

HRID 239188 reaction equation
F[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](O)=[O:22])[N:9]=2)=[CH:4][CH:3]=1.[CH3:24]CN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[Br:55][C:56]1[S:57][C:58]2[CH2:64][CH2:63][NH:62][CH2:61][CH2:60][C:59]=2[N:65]=1>CN(C=O)C>[Br:55][C:56]1[S:57][C:58]2[CH2:64][CH2:63][N:62]([C:21](=[O:22])[CH2:20][N:10]3[C:11]([C:13]4[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=4)=[N:12][C:8]([C:5]4[CH:4]=[CH:3][C:2]([CH3:24])=[CH:7][CH:6]=4)=[N:9]3)[CH2:61][CH2:60][C:59]=2[N:65]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 866864842-Bromo-5,6,7,8-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 866865211-(2-Bromo-4,5,7,8-tetrahydro-thiazolo[4,5-d]azepin-6-yl)-2-(5-(4-fluoro-phenyl)-3-p-tolyl-(1,2,4)triazol-1-yl)-ethanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

151 mg (3,5-bis-(4-fluoro-phenyl)-(1,2,4)triazol-1-yl)-acetic acid and 84 μL DIPEA were dissolved in 2.5 mL DMF. 154 mg TBTU was added to this solution and the mixture was stirred for 10 min. at RT. Then, 112 mg 2-bromo-5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepine in 2.5 mL DMF was added. The mixture was stirred for 2 h at RT. The reaction-solution was purified by HPLC to yield 19.8 mg of the desired compound. Rt: 2.21 (method I), (M+H)+: 530/32

Workup

  1. stirringThe mixture was stirred for 2 h at RT
  2. customThe reaction-solution was purified by HPLC

Sources & evidence

ORD record
ord-8ace7d62387b47c3b11c4db2425f4cdf
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

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