Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 66940416, compound

HRID 1845019Notes

Reaction equation

HRID 1845019 reaction equation
[CH3:1][O:2][C:3]1[C:4]2[N:5]([CH:9]=[C:10](C(O)=O)[N:11]=2)[CH:6]=[CH:7][CH:8]=1.CN([C:18]([O:22]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:39]1[CH:43]=[CH:42][N:41]=[C:40]1[NH:44][C:45]([C:47]1[C:55]2[NH:54][C:53]([NH2:56])=[N:52][C:51]=2[CH:50]=[CH:49][CH:48]=1)=[O:46]>CN(C=O)C.CCN(C(C)C)C(C)C.[Cl-].[Na+].O>[NH:41]1[CH:42]=[CH:43][N:39]=[C:40]1[NH:44][C:45]([C:47]1[C:55]2[N:54]=[C:53]([NH:56][C:18]([C:9]3[N:5]4[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]4=[N:11][CH:10]=3)=[O:22])[NH:52][C:51]=2[CH:50]=[CH:49][CH:48]=1)=[O:46]

Participants

7

Reactant 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 669402468-Methoxyimidazo[1,2-a]pyridine-2-carboxylic acidHCID 178508178HCID 178508178, compound2×

Product 1

HCID 66940416HCID 66940416, compoundYield 40%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 81531DiisopropylethylamineSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

300 mg (3.0 mmol) of the above 8-methoxy-imidazo[1,2-a]pyridine-2-carboxylic acid and 200 mg (0.5 mmol) of HBTU in a mixture of 1.5 mL of DMF and 0.6 mL of DIEA was reacted with 60 mg (0.25 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 41 mg (40%) of 2-[(8-methoxy-imidazo[1,2-a]pyridine-3-carbonyl)-amino]-1H-benzoimidazole-4-carboxylic acid (1H-imidazol-2-yl)-amide as a solid. LCMS: 417 (M+1)+.

Workup

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

Sources & evidence

ORD record
ord-d0bb6cfd6e5545d99411b02a23ef3254
Source dataset
uspto-grants-2015_02
Patent number
US08946259B2

Reaction notes

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