HCID 58431111, compound → HCID 42632961, compound

HRID 1040562Notes

Reaction equation

HRID 1040562 reaction equation
COC1C=CC(C[N:8](CC2C=CC(OC)=CC=2)[C:9]2[N:14]=[C:13]([C:15]3([NH:18][C:19]([C:21]4([NH:24][C:25]([C:27]5[N:31]6[C@:32]([CH3:56])([CH2:44][C:45]7[CH:50]=[CH:49][C:48]([O:51][C:52]([F:55])([F:54])[F:53])=[CH:47][CH:46]=7)[C:33](=[O:43])[N:34]([C:35]7[CH:40]=[C:39]([Cl:41])[CH:38]=[C:37]([Cl:42])[CH:36]=7)[C:30]6=[N:29][CH:28]=5)=[O:26])[CH2:23][CH2:22]4)=[O:20])[CH2:17][CH2:16]3)[CH:12]=[CH:11][CH:10]=2)=CC=1>FC(F)(F)C(O)=O>[NH2:8][C:9]1[N:14]=[C:13]([C:15]2([NH:18][C:19]([C:21]3([NH:24][C:25]([C:27]4[N:31]5[C@:32]([CH3:56])([CH2:44][C:45]6[CH:46]=[CH:47][C:48]([O:51][C:52]([F:53])([F:55])[F:54])=[CH:49][CH:50]=6)[C:33](=[O:43])[N:34]([C:35]6[CH:40]=[C:39]([Cl:41])[CH:38]=[C:37]([Cl:42])[CH:36]=6)[C:30]5=[N:29][CH:28]=4)=[O:26])[CH2:22][CH2:23]3)=[O:20])[CH2:17][CH2:16]2)[CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 1

HCID 58431111HCID 58431111, compound

Product 1

HCID 42632961HCID 42632961, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (R)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-5-(4-trifluoromethoxy-benzyl)-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carboxylic acid [1-(1-{6-[bis-(4-methoxy-benzyl)-amino]-pyridin-2-yl}-cyclopropylcarbamoyl)-cyclopropyl]-amide (80 mg, 0.084 mmol) in trifluoroacetic acid (2 mL) was stirred at room temperature for 4 h. The solvent was removed under a stream of N2 and the residue was partitioned between EtOAc (4 mL) and saturated aqueous NaHCO3 (4 mL). The layers were separated and the aqueous layer was further extracted with EtOAc (2×4 mL). The combined organics were evaporated in vacuo, and the residue was purified via reverse phase HPLC. The purified material was then passed through a basic amino group functionalized solid phase extraction cartridge to give 31 mg (51%) of the title compound as a white solid, m/z 715.0 [M+2]+.

Workup

  1. customThe solvent was removed under a stream of N2
  2. customthe residue was partitioned between EtOAc (4 mL) and saturated aqueous NaHCO3 (4 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was further extracted with EtOAc (2×4 mL)
  5. customThe combined organics were evaporated in vacuo
  6. customthe residue was purified via reverse phase HPLC
  7. extractionThe purified material was then passed through a basic amino group functionalized solid phase extraction cartridge

Sources & evidence

ORD record
ord-39b26563b513433c8e6c5b00abff50e6
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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