Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 178520839, compound

HRID 1844948Notes

Reaction equation

HRID 1844948 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](O)=[O:21])=[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.[NH2:47][CH:48]([CH:58]1[CH2:60][CH2:59]1)[CH2:49][C:50]([NH:52][C:53]1[NH:54][CH:55]=[CH:56][N:57]=1)=[O:51]>>[CH:58]1([CH:48]([NH:47][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:21])[CH2:49][C:50](=[O:51])[NH:52][C:53]2[NH:54][CH:55]=[CH:56][N:57]=2)[CH2:60][CH2:59]1

Participants

4

Reactant 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66940190HCID 66940190, compoundHCID 178524149HCID 178524149, compound

Product 1

HCID 178520839HCID 178520839, compoundYield 4.3%

Procedure

289 mg (1 mmol) of 2-isoquinolin-3-yl-1H-benzoimidazole-5-carboxylic acid (289 mg, 1 mmol) was reacted with 380 mg (1 mmol) of HBTU and 3-amino-3-cyclopropyl-N-(1H-imidazol-2-yl)-propionamide (230 mg, 1 mmol) as described in general procedure A. A solid precipitated from the solution and was collected by filtration, washed with H2O and Et2O, to give 2-isoquinolin-3-yl-1H-benzoimidazole-5-carboxylic acid [1-cyclopropyl-2-(1H-imidazol-2-ylcarbamoyl)-ethyl]-amide (20 mg, 4%). LCMS: 466 (M+1)+. 1H NMR (DMSO-d6, 400 MHz): δ 9.20 (s, 1H), 8.56 (s, 1H), 8.09-7.34 (m, 9H), 6.39 (s, 2H), 3.71 (t, 1H), 2.44 (m, 2H), 0.81 (m, 1H), 0.10 (m, 4H) ppm.

Workup

  1. customA solid precipitated from the solution
  2. filtrationwas collected by filtration
  3. washwashed with H2O and Et2O

Sources & evidence

ORD record
ord-d2b0e093e2794ae7904dc74388cd1a19
Source dataset
uspto-grants-2015_02
Patent number
US08946259B2

Reaction notes

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