Diisopropylethylamine → HCID 58026393, compound

HRID 1910185Notes

Reaction equation

HRID 1910185 reaction equation
[O:1]([C:8]1[CH:9]=[N:10][CH:11]=[C:12]([CH:16]=1)[C:13]([OH:15])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH:50]1[CH:54]=[CH:53][N:52]=[C:51]1[NH:55][C:56]([C:58]1[C:66]2[NH:65][C:64]([NH2:67])=[N:63][C:62]=2[CH:61]=[CH:60][CH:59]=1)=[O:57]>O.CN(C=O)C>[NH:52]1[CH:53]=[CH:54][N:50]=[C:51]1[NH:55][C:56]([C:58]1[C:66]2[N:65]=[C:64]([NH:67][C:13]([C:12]3[CH:11]=[N:10][CH:9]=[C:8]([O:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH:16]=3)=[O:15])[NH:63][C:62]=2[CH:61]=[CH:60][CH:59]=1)=[O:57]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 60094554HCID 60094554, compoundHCID 178508178HCID 178508178, compound2×

Product 1

HCID 58026393HCID 58026393, compoundYield 11.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

0.07 g (0.30 mmol) of 5-phenoxy-nicotinic acid and 0.12 g (0.32 mmol) of HBTU were combined in a flask charged with 2 mL of DMF and 0.25 mL of DIEA. The reaction mixture was then treated with 0.05 g (0.20 mmol) of 2-amino-3H-benzoimidazole-4-carboxylic acid (1H-imidazol-2-yl)-amide (Intermediate B) and stirred at 80° C. for 1 h. The reaction mixture was diluted with water, and the resultant solid precipitate was filtered and washed with saturated NaHCO3. The solid was dissolved with MeOH, evaporated onto silica gel and isolated by flash column chromatography (500 mL DCM/20 mL NH3/MeOH) to yield 10 mg (11%) of 2-[(5-phenoxy-pyridine-3-carbonyl)-amino]-1H-benzoimidazole-4-carboxylic acid (1H-imidazol-2-yl)-amide. LCMS: 441 (M+1)+.

Workup

  1. filtrationthe resultant solid precipitate was filtered
  2. washwashed with saturated NaHCO3
  3. dissolutionThe solid was dissolved with MeOH
  4. customevaporated onto silica gel
  5. customisolated by flash column chromatography (500 mL DCM/20 mL NH3/MeOH)

Sources & evidence

ORD record
ord-867d9fff90894110a4ee7de9192b82f3
Source dataset
uspto-grants-2013_12
Patent number
US08598353B2

Reaction notes

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