Trifluoroacetic acid → HCID 19063690, compound

HRID 482352Notes

Reaction equation

HRID 482352 reaction equation
C([O:5][C:6](=[O:48])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]([NH:16][CH:17]2[C:23](=[O:24])[N:22]([C:25]([CH:35]([CH3:37])[CH3:36])([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:26](=[O:28])[NH2:27])[C:21]3[CH:38]=[CH:39][CH:40]=[CH:41][C:20]=3[C:19]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[N:18]2)=[O:15])[CH:8]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH:35]([C:25]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:26](=[O:28])[NH2:27])[N:22]1[C:21]2[CH:38]=[CH:39][CH:40]=[CH:41][C:20]=2[C:19]([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)=[N:18][CH:17]([NH:16][C:14](=[O:15])[NH:13][C:9]2[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=2)[C:6]([OH:48])=[O:5])[C:23]1=[O:24])([CH3:37])[CH3:36]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86753038HCID 86753038, compound

Product 1

HCID 19063690HCID 19063690, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-{3-[1-(Isopropyl-phenyl-carbamoylmethyl)-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl]-ureido}-benzoic acid tert-butyl ester (145 mg, 0.225 mmol), prepared as in Example 5A, in anhydrous DCM (2 mL) at 0-5--C. under nitrogen is treated with triflouroacetic acid (2 mL). After stirring for 2 hrs., the reaction mixture is concentrated in vacuo and triturated with anhydrous ether. The resulting slurry is filtered and the product dried overnight under high vacuum at ambient temperature to provide the title compound as a crystalline solid (80 mg, 0.136 mmol). 1H NMR (300 MHz, d6-DMSO) δ=0.96 (d, J=6.8 Hz, 6H); 4.12 (d, J=16.6 Hz, 1H); 4.23 (d, J=16.6 Hz, 1H); 4.71-6.76 (m, 1H); 5.18-5.27 (m, 1H); 7.24-7.70 (m, 19H); 8.02 (b, 1H); 9.22 (b, 1H). MS (FAB): [M+H]+ =590.

Workup

  1. concentration, the reaction mixture is concentrated in vacuo
  2. customtriturated with anhydrous ether
  3. filtrationThe resulting slurry is filtered
  4. customthe product dried overnight under high vacuum at ambient temperature

Sources & evidence

ORD record
ord-806b256a744b43588b878424b5fd3c4d
Source dataset
uspto-grants-1998_08
Patent number
US05795887

Reaction notes

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