1,1'-Carbonyldiimidazole → HCID 71288134, compound

HRID 1497911Notes

Reaction equation

HRID 1497911 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([C:15]([OH:17])=O)[CH2:12][C:11]([F:14])([F:13])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.O[N:31]=[C:32]([C:34]1[CH:35]=[CH:36][C:37]([CH3:52])=[C:38]([NH:40][C:41]([C:43]2[N:47]3[CH:48]=[CH:49][CH:50]=[CH:51][C:46]3=[N:45][CH:44]=2)=[O:42])[CH:39]=1)[NH2:33]>CN1C(=O)CCC1.C(OCC)(=O)C.O>[F:14][C:11]1([F:13])[CH2:10][C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])([C:15]2[O:17][N:31]=[C:32]([C:34]3[CH:35]=[CH:36][C:37]([CH3:52])=[C:38]([NH:40][C:41]([C:43]4[N:47]5[CH:48]=[CH:49][CH:50]=[CH:51][C:46]5=[N:45][CH:44]=4)=[O:42])[CH:39]=3)[N:33]=2)[CH2:12]1

Participants

7

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 69928906Cyclobutanecarboxylic acid, 1-[[(1,1-dimethylethoxy)carbonyl]amino]-3,3-difluoro-HCID 86677441N-(5-(N'-hydroxycarbamimidoyl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide

Product 1

HCID 71288134HCID 71288134, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

To a stirring solution of 1-((tert-butoxycarbonyl)amino)-3,3-difluorocyclobutanecarboxylic acid (164) (45 mg, 0.18 mmol) in anhydrous NMP (1.3 mL) was added 1,1′-carbonyldiimidazole (CDI) (29 mg, 0.18 mmol). The reaction was stirred for 3 minutes. N-(5-(N′-hydroxycarbamimidoyl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (9) (69 mg, 0.22 mmol) was added and the reaction was stirred for 25 minutes. Then, the reaction was heated at 120° C. for 15 minutes. The crude product was taken up in ethyl acetate and water. The organic was washed with 2× water/brine mixture and dried over magnesium sulfate. The solvent was concentrated and the crude product was purified using silica gel chromatography using 60% ethyl acetate/hexanes to afford tert-butyl (3,3-difluoro-1-(3-(3-(imidazo[1,2-a]pyridine-3-carboxamido)-4-methylphenyl)-1,2,4-oxadiazol-5-yl)cyclobutyl)carbamate (165). MS m/z 525.2 (M+1)+

Workup

  1. stirringthe reaction was stirred for 25 minutes
  2. washThe organic was washed with 2× water/brine mixture
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe solvent was concentrated
  5. customthe crude product was purified

Sources & evidence

ORD record
ord-cca38b70453e4562bb540a00ec1b8c72
Source dataset
uspto-grants-2015_12
Patent number
US09199981B2

Reaction notes

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