Dichloromethane → HCID 42635287, compound

HRID 1040574Notes

Reaction equation

HRID 1040574 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([C:15]2([NH:18][C:19]([C:21]3([NH:24][C:25]([C:27]4[N:31]5[C@@:32]([CH2:45][C:46]6[CH:51]=[CH:50][C:49]([C:52]#[N:53])=[CH:48][CH:47]=6)([CH3:44])[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])[CH2:23][CH2:22]3)=[O:20])[CH2:17][CH2:16]2)[CH:10]=1)(C)(C)C.C(Cl)Cl.C(O)(C(F)(F)F)=O>CO.C(Cl)Cl>[NH2:7][CH2:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([C:15]2([NH:18][C:19]([C:21]3([NH:24][C:25]([C:27]4[N:31]5[C@@:32]([CH2:45][C:46]6[CH:51]=[CH:50][C:49]([C:52]#[N:53])=[CH:48][CH:47]=6)([CH3:44])[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])[CH2:16][CH2:17]2)[CH:10]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 58430888HCID 58430888, compound

Product 1

HCID 42635287HCID 42635287, compoundYield 164.3%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

(2-{1-[(1-{[(R)-5-(4-Cyano-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-cyclopropanecarbonyl)-amino]-cyclopropyl}-pyridin-4-ylmethyl)-carbamic acid tert-butyl ester (45 mg, 0.06 mmol) was placed in RBF with CH2Cl2 and TFA was added. The reaction was diluted with 10 mL 10% MeOH/CH2Cl2 and washed with water (2×5 mL). The organic layer was separated, dried (MgSO4), and concentrated. Reverse Phase HPLC purification (30-100% CH3CN/H2O as gradient) yielded 66 mg of the title compound as a bis-TFA salt, m/z=669.5 [M+1]+.

Workup

  1. additionwas added
  2. washwashed with water (2×5 mL)
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customReverse Phase HPLC purification (30-100% CH3CN/H2O as gradient)

Sources & evidence

ORD record
ord-5d2500feadfb42b4a4c23266b5b24c3d
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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