Sodium Bicarbonate → HCID 58026530, compound

HRID 1910189Notes

Reaction equation

HRID 1910189 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]([OH:17])=O)[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:42]1[CH:46]=[CH:45][N:44]=[C:43]1[NH:47][C:48]([C:50]1[C:58]2[NH:57][C:56]([NH2:59])=[N:55][C:54]=2[CH:53]=[CH:52][CH:51]=1)=[O:49].C([O-])(O)=O.[Na+]>CN(C=O)C.CCN(C(C)C)C(C)C.O>[NH:44]1[CH:45]=[CH:46][N:42]=[C:43]1[NH:47][C:48]([C:50]1[C:58]2[N:57]=[C:56]([NH:59][C:15]([C:11]3[CH:10]=[C:9]([C:8]#[C:7][C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH:14]=[CH:13][N:12]=3)=[O:17])[NH:55][C:54]=2[CH:53]=[CH:52][CH:51]=1)=[O:49]

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66940522HCID 66940522, compoundHCID 178508178HCID 178508178, compound2×

Product 1

HCID 58026530HCID 58026530, compoundYield 43%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 81531DiisopropylethylamineSolvent

Procedure

0.05 (0.23 mmol) of the above synthesized 4-phenylethynyl-pyridine-2-carboxylic acid, 0.095 g (0.25 mmol) of HBTU in a mixture of 2.0 ml of DMF and 0.20 mL of DIEA was reacted with 0.05 g (0.20 mmol) of 2-amino-3H-benzoimidazole-4-carboxylic acid (1H-imidazol-2-yl)-amide (Intermediate B) as described in general procedure A. The reaction mixture was cooled to r.t. 5.0 mL of water and 5.0 mL of saturated NaHCO3 was added, and the resulting solid was filtered. The solid was washed with water and ether, and dried to provide 0.04 g (43%) of 2-[(4-phenylethynyl-pyridine-2-carbon-yl)-amino]-1H-benzoimidazole-4-carboxylic acid (1H-imidazol-2-yl)-amide. LCMS: 448 (M+1)+.

Workup

  1. filtrationthe resulting solid was filtered
  2. washThe solid was washed with water and ether
  3. customdried

Sources & evidence

ORD record
ord-d720703dc92446f2b957ad0ee39316bb
Source dataset
uspto-grants-2013_12
Patent number
US08598353B2

Reaction notes

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