Trifluoroacetic acid → HCID 178464158, compound

HRID 1919184Notes

Reaction equation

HRID 1919184 reaction equation
CN(C(ON1N=N[C:11]2[CH:12]=[CH:13][CH:14]=N[C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:25]([N:27]([CH2:38][CH3:39])[C@H:28]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:29](O)=[O:30])[CH3:26].[NH:40]1[CH2:44][CH2:43][CH2:42][C@H:41]1[C:45]1[NH:46][CH:47]=[C:48]([CH2:50][CH2:51][C:52]2[CH:57]=[CH:56][C:55]([CH2:58][CH2:59][C:60]3[NH:64][C:63]([C@@H:65]4[CH2:69][CH2:68][CH2:67][NH:66]4)=[N:62][CH:61]=3)=[CH:54][CH:53]=2)[N:49]=1.C(O)(C(F)(F)F)=[O:71].[CH3:77][CH2:78][N:79]([CH:83]([CH3:85])C)[CH:80]([CH3:82])[CH3:81]>CN(C=O)C.CO>[CH2:83]([N:79]([CH2:78][CH3:77])[C@H:80]([C:81]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:82]([N:66]1[CH2:67][CH2:68][CH2:69][C@H:65]1[C:63]1[NH:64][C:60]([CH2:59][CH2:58][C:55]2[CH:54]=[CH:53][C:52]([CH2:51][CH2:50][C:48]3[N:49]=[C:45]([C@@H:41]4[CH2:42][CH2:43][CH2:44][N:40]4[C:29](=[O:30])[C@@H:28]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[N:27]([CH2:38][CH3:39])[CH2:25][CH3:26])[NH:46][CH:47]=3)=[CH:57][CH:56]=2)=[CH:61][N:62]=1)=[O:71])[CH3:85]

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 1091378(R)-2-(diethylamino)-2-phenylacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178420207HCID 178420207, compound

Product 1

HCID 178464158HCID 178464158, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×

Procedure

HATU (76 mg, 0.2 mmole) was added to a stirred solution of (R)-2-(diethylamino)-2-phenylacetic acid (49 mg, 0.2 mmole) in DMF (1 mL) and DIEA (0.14 mL) and the mixture was stirred for 5 minutes. The 1-(2-(2-((S)-pyrrolidin-2-yl)-1H-imidazol-4-yl)ethyl)-4-(2-(2-((S)-pyrrolidin-2-yl)-1H-imidazol-5-yl)ethyl)benzene (40 mg) in DMF (1 mL) was added and the reaction mixture was stirred under argon for 16 hrs. The reaction mixture was purified directly by prep HPLC. The solid obtained, the TFA salt, was loaded onto an SCX ion exchange cartridge with methanol, then the product was isolated as the free base by eluting with a solution of 2 M NH3 in methanol to yield (1R)-2-((2S)-2-(4-(2-(4-(2-(2-((2S)-1-((2R)-2-(diethylamino)-2-phenylacetyl)-2-pyrrolidinyl)-1H-imidazol-5-yl)ethyl)phenyl)ethyl)-1H-imidazol-2-yl)-1-pyrrolidinyl)-N,N-diethyl-2-oxo-1-phenylethanamine (40 mg) as a white solid.

Workup

  1. stirringthe reaction mixture was stirred under argon for 16 hrs
  2. customThe reaction mixture was purified directly by prep HPLC
  3. customThe solid obtained
  4. customthe product was isolated as the free base
  5. washby eluting with a solution of 2 M NH3 in methanol

Sources & evidence

ORD record
ord-3d8b135d3fab49179fa8f38e79b3bec7
Source dataset
uspto-grants-2013_12
Patent number
US08618153B2

Reaction notes

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