Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 178522469, compound

HRID 1367840Notes

Reaction equation

HRID 1367840 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]2[NH:15][C:14]3[CH:16]=[CH:17][C:18]([C:20]([OH:22])=O)=[CH:19][C:13]=3[N:12]=2)[N:2]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[NH:48]1[CH:52]=[CH:51][N:50]=[C:49]1[NH:53][C:54]([C:56]1([NH2:61])[CH2:60][CH2:59][CH2:58][CH2:57]1)=[O:55]>>[NH:48]1[CH:52]=[CH:51][N:50]=[C:49]1[NH:53][C:54]([C:56]1([NH:61][C:20]([C:18]2[CH:17]=[CH:16][C:14]3[NH:15][C:11]([C:3]4[N:2]=[CH:1][C:10]5[C:5]([CH:4]=4)=[CH:6][CH:7]=[CH:8][CH:9]=5)=[N:12][C:13]=3[CH:19]=2)=[O:22])[CH2:60][CH2:59][CH2:58][CH2:57]1)=[O:55]

Participants

4

Reactant 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66940335HCID 66940335, compoundHCID 178524149HCID 178524149, compound

Product 1

HCID 178522469HCID 178522469, compoundYield 10.3%

Procedure

145 mg (0.5 mmol) of 2-isoquinolin-3-yl-1H-benzoimidazole-5-carboxylic acid (Synthesized in Example 1, step 3) was reacted with 280 mg (0.75 mmol) of HBTU and 1-amino-cyclopentanecarboxylic acid (1H-imidazol-2-yl)-amide HCl salt (120 mg, 0.5 mmol) as described in general procedure A. A solid precipitated from the solution and was collected by filtration, washed with H2O and EtOAc, to give 2-isoquinolin-3-yl-1H-benzoimidazole-5-carboxylic acid [1-(1H-imidazol-2-ylcarbamoyl)-cyclopentyl]-amide (24 mg, 10%). LCMS: 466 (M+1)+.

Workup

  1. customA solid precipitated from the solution
  2. filtrationwas collected by filtration
  3. washwashed with H2O and EtOAc

Sources & evidence

ORD record
ord-78b2cf95e7f140b69a8211a16711bed7
Source dataset
uspto-grants-2011_02
Patent number
US07893267B2

Reaction notes

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