1,1'-Carbonyldiimidazole → HCID 66634907, compound

HRID 510113Notes

Reaction equation

HRID 510113 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[C:6]([NH2:9])[N:5]=[C:4]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[N:12]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])[N:11]=2)[N:3]=1.C(N(CC)C(C)C)(C)C.[C:36](N1C=CN=C1)(N1C=CN=C1)=[O:37]>CN(C)C=O>[NH2:9][C:6]1[C:7]2[O:8][C:36](=[O:37])[NH:1][C:2]=2[N:3]=[C:4]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[N:12]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])[N:11]=2)[N:5]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 136364529HCID 136364529, compound

Product 1

HCID 66634907HCID 66634907, compoundYield 52.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

159 mg (0.453 mmol) of the compound prepared in example 58A in dimethylformamide (10 ml) were admixed with 94 μl (0.543 mmol) of N,N-diisopropylethylamine and 88 mg (0.543 mmol) of carbonyldiimidazole, and the mixture was stirred at RT overnight. The mixture was filtered, the filtrate was concentrated and the residue was purified by means of preparative HPLC (acetonitrile:water (+0.05% formic acid) gradient). 90 mg of the title compound were obtained (52% of theory).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified by means of preparative HPLC (acetonitrile:water (+0.05% formic acid) gradient)

Sources & evidence

ORD record
ord-0ed241d160c34e2c870057e5f5c41d72
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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