O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → HCID 59292885, compound

HRID 2409649Notes

Reaction equation

HRID 2409649 reaction equation
Cl.[CH3:2][N:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([NH2:16])=[N:14][CH:15]=2)[CH2:5][CH2:4]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[S:39]1[CH:43]=[C:42]([C:44]2[C:53]3[N:52]=[CH:51][CH:50]=[N:49][C:48]=3[C:47]([C:54](O)=[O:55])=[CH:46][CH:45]=2)[C:41]2[CH:57]=[CH:58][CH:59]=[CH:60][C:40]1=2.S1C2C=CC=CC=2C(B(O)O)=C1>C(Cl)Cl.CO>[CH3:2][N:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([NH:16][C:54]([C:47]3[C:48]4[N:49]=[CH:50][CH:51]=[N:52][C:53]=4[C:44]([C:42]4[C:41]5[CH:57]=[CH:58][CH:59]=[CH:60][C:40]=5[S:39][CH:43]=4)=[CH:45][CH:46]=3)=[O:55])=[N:14][CH:15]=2)[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2776344(1-Benzothiophen-3-yl)boronic acidHCID 669145625-(4-Methyl-piperazin-1-ylmethyl)-pyridin-2-ylamine hydrochlorideHCID 669146368-Benzo[b]thiophen-3-yl-quinoxaline-5-carboxylic acid

Product 1

HCID 59292885HCID 59292885, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared in analogy to the procedure described in Step 14.1 but stirring the reaction mixture at rt overnight and using 2 equiv of 5-(4-methyl-piperazin-1-ylmethyl)-pyridin-2-ylamine hydrochloride (Example 31), TBTU (2 equiv) and 8-benzo[b]thiophen-3-yl-quinoxaline-5-carboxylic acid. The carboxylic acid was synthesized as described in Steps 1.2-1.7 but using benzothiophene-3-boronic acid in Step 1.4. Title compound: ESI-MS: 494.9 [M+H]+; tR=3.77 min (System 1); TLC: Rf=0.17 (DCM/MeOH, 9:1).

Workup

  1. customThe title compound was prepared in analogy to the procedure

Sources & evidence

ORD record
ord-427f04d369e34a6fb02564b03088a5a3
Source dataset
uspto-grants-2014_08
Patent number
US08815901B2

Reaction notes

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