Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 58026485, compound

HRID 1910180Notes

Reaction equation

HRID 1910180 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]2[CH:9]=[CH:8][CH:7]=[CH:6][N:5]2[C:10]=1[C:11]([OH:13])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:38]1[CH:42]=[CH:41][N:40]=[C:39]1[NH:43][C:44]([C:46]1[C:54]2[NH:53][C:52]([NH2:55])=[N:51][C:50]=2[CH:49]=[CH:48][CH:47]=1)=[O:45]>CN(C=O)C.CCN(C(C)C)C(C)C.[Cl-].[Na+].O>[NH:40]1[CH:41]=[CH:42][N:38]=[C:39]1[NH:43][C:44]([C:46]1[C:54]2[N:53]=[C:52]([NH:55][C:11]([C:10]3[N:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]4=[N:3][C:2]=3[CH3:1])=[O:13])[NH:51][C:50]=2[CH:49]=[CH:48][CH:47]=1)=[O:45]

Participants

7

Reactant 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66940493HCID 66940493, compoundHCID 178508178HCID 178508178, compound2×

Product 1

HCID 58026485HCID 58026485, compoundYield 17.8%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 81531DiisopropylethylamineSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

100 mg (0.56 mmol) of the 2-methyl-1,8a-dihydro-imidazo[1,2-a]pyridine-3-carboxylic acid and 234 mg (0.61 mmol) of HBTU in a mixture of 1.5 mL of DMF and 0.6 mL of DIEA was reacted with 137 mg (0.56 mmol) of the 2-amino-3H-benzoimidazole-4-carboxylic acid (1H-imidazol-2-yl)-amide (Intermediate B) as described in general procedure A. After the reaction was complete, it was diluted with brine (20 mL), and the resulting solid was filtered, washed with water, ethyl acetate and dried under vacuum to give 40 mg (17%) of 2-[(2-methyl-imidazo[1,2-a]pyridine-3-carbonyl)-amino]-1H-benzoimidazole-4-carboxylic acid (1H-imidazol-2-yl)-amide as a solid. LCMS: 401 (M+1)+.

Workup

  1. filtrationthe resulting solid was filtered
  2. washwashed with water, ethyl acetate
  3. customdried under vacuum

Sources & evidence

ORD record
ord-95ae37d554434af7ba8ed22dc6c01d28
Source dataset
uspto-grants-2013_12
Patent number
US08598353B2

Reaction notes

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