Bis(2-amino-1H-imidazole) sulphate → HCID 178522543, compound

HRID 1910132Notes

Reaction equation

HRID 1910132 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]([NH:13][C:14]2[NH:18][C:17]3[CH:19]=[CH:20][C:21]([C:23]([OH:25])=O)=[CH:22][C:16]=3[N:15]=2)=[O:12])[N:2]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.S(O)(O)(=O)=O.[NH2:55][C:56]1[NH:57][CH:58]=[CH:59][N:60]=1>CN(C=O)C.CCN(C(C)C)C(C)C.O>[NH:57]1[CH:58]=[CH:59][N:60]=[C:56]1[NH:55][C:23]([C:21]1[CH:20]=[CH:19][C:17]2[NH:18][C:14]([NH:13][C:11]([C:3]3[N:2]=[CH:1][C:10]4[C:5]([CH:4]=3)=[CH:6][CH:7]=[CH:8][CH:9]=4)=[O:12])=[N:15][C:16]=2[CH:22]=1)=[O:25]

Participants

7

Reactant 3

HCID 135136Bis(2-amino-1H-imidazole) sulphateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178524177HCID 178524177, compound

Product 1

HCID 178522543HCID 178522543, compoundYield 5.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 81531DiisopropylethylamineSolvent

Procedure

0.15 g (0.45 mmol) of 2-[(isoquinoline-3-carbonyl)-amino]-1H-benzoimidazole-5-carboxylic acid was reacted with 0.26 g (0.68 mmol) of HBTU and 0.06 g (0.45 mmol) of 2-aminoimidazole sulfate in 3.0 mL of DMF and 1.0 mL of DIEA as described in general procedure A. After cooling to room temperature, the reaction mixture was diluted with water, the solid was collected by filtration, dissolved with MeOH and evaporated onto silica gel, and isolated by flash column chromatography (500 mL DCM/20 mL NH3/MeOH) to yield ˜10 mg of the desired isoquinoline-3-carboxylic acid [5-(1H-imidazol-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-amide. LCMS: 398.0 (M+1)+

Workup

  1. filtrationthe solid was collected by filtration
  2. dissolutiondissolved with MeOH
  3. customevaporated onto silica gel
  4. customisolated by flash column chromatography (500 mL DCM/20 mL NH3/MeOH)

Sources & evidence

ORD record
ord-82f185965cf7429d88d3e99df7d9b1ea
Source dataset
uspto-grants-2013_12
Patent number
US08598353B2

Reaction notes

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