Cyclopropanecarboxylic acid → HCID 67390530, compound

HRID 1040573Notes

Reaction equation

HRID 1040573 reaction equation
[CH:1]1([C:4](O)=[O:5])[CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.Cl.[NH2:33][CH2:34][C:35]1[CH:40]=[CH:39][N:38]=[C:37]([C:41]2([NH:44][C:45]([C:47]3([NH:50][C:51]([C:53]4[N:57]5[C@@:58]([CH2:71][C:72]6[CH:77]=[CH:76][C:75]([C:78]#[N:79])=[CH:74][CH:73]=6)([CH3:70])[C:59](=[O:69])[N:60]([C:61]6[CH:66]=[C:65]([Cl:67])[CH:64]=[C:63]([Cl:68])[CH:62]=6)[C:56]5=[N:55][CH:54]=4)=[O:52])[CH2:49][CH2:48]3)=[O:46])[CH2:43][CH2:42]2)[CH:36]=1.CCN(C(C)C)C(C)C>CN(C=O)C.C(#N)C.O>[CH:1]1([C:4]([NH:33][CH2:34][C:35]2[CH:40]=[CH:39][N:38]=[C:37]([C:41]3([NH:44][C:45]([C:47]4([NH:50][C:51]([C:53]5[N:57]6[C@@:58]([CH2:71][C:72]7[CH:77]=[CH:76][C:75]([C:78]#[N:79])=[CH:74][CH:73]=7)([CH3:70])[C:59](=[O:69])[N:60]([C:61]7[CH:66]=[C:65]([Cl:67])[CH:64]=[C:63]([Cl:68])[CH:62]=7)[C:56]6=[N:55][CH:54]=5)=[O:52])[CH2:48][CH2:49]4)=[O:46])[CH2:42][CH2:43]3)[CH:36]=2)=[O:5])[CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 15655Cyclopropanecarboxylic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86657596HCID 86657596, compound

Product 1

HCID 67390530HCID 67390530, compoundYield 70.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

Cyclopropanecarboxylic acid (0.00903 mL, 0.108 mmol) and HATU (25.605 mg, 0.0673 mmol) were dissolved in dry DMF (1 mL). Stirred for 5 min. To this solution was added (R)-5-(4-Cyano-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carboxylic acid {1-[1-(4-aminomethyl-pyridin-2-yl)-cyclopropylcarbamoyl]-cyclopropyl}-amide dihydrochloric acid salt (40 mg, 0.0539 mmol) followed by DIPEA (0.038 mL, 0.215 mmol). Stirred at room temperature for 30 min. Diluted with ACN (1 mL) and water (1 mL) and filtered. The crude product was purified by reverse phase HPLC using 20-95% ACN/water as the gradient. Solvent was evaporated. The resultant product was redissolved in 10% MeOH/DCM and filtered through a basic (NH2) cartridge. Solvent was evaporated to afford 28.1 mg of the title compound as a white solid, m/z 737.7 [M+1]+.

Workup

  1. stirringStirred at room temperature for 30 min
  2. filtrationfiltered
  3. customThe crude product was purified by reverse phase
  4. customSolvent was evaporated
  5. dissolutionThe resultant product was redissolved in 10% MeOH/DCM
  6. filtrationfiltered through a basic (NH2) cartridge
  7. customSolvent was evaporated

Sources & evidence

ORD record
ord-14d14375139e421289f5e42627840af6
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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