HCID 66887685, compound → HCID 49854434, compound

HRID 1895558Notes

Reaction equation

HRID 1895558 reaction equation
[NH2:1][C:2]1[C:7]([C:8](=[O:10])[NH2:9])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:11][C:12]([CH:14]1[CH2:23][C:22]2[C:17](=[CH:18][C:19]([NH:24][C:25]([O:27]C(C)(C)C)=[O:26])=[CH:20][CH:21]=2)[CH2:16][N:15]1[C:32]([O:34]C(C)(C)C)=[O:33])=O>C(O)(=O)C>[C:7]([O:27][C:25]([NH:24][C:19]1[CH:18]=[C:17]2[C:22]([CH2:23][CH:14]([C:12]3[NH:11][C:3]4[CH:4]=[CH:5][CH:6]=[C:7]([C:8](=[O:10])[NH2:9])[C:2]=4[N:1]=3)[N:15]([C:32]([O:34][C:17]([CH3:22])([CH3:18])[CH3:16])=[O:33])[CH2:16]2)=[CH:21][CH:20]=1)=[O:26])([CH3:8])([CH3:2])[CH3:6]

Participants

3

Reactant 1

HCID 66887685HCID 66887685, compound

Product 1

HCID 49854434HCID 49854434, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Step-3: A solution of tert-butyl 3-((2-amino-3-carbamoylphenyl)carbamoyl)-7-((tert-butoxycarbonyl)amino)-3,4-dihydroisoquinoline-2(1H)-carboxylate (70 mg, 0.133 mmol) in acetic acid (2 ml) was heated to 80° C. and stirred for 2.5 h. The reaction mixture was concentrated, neutralized with aq. NaHCO3 and extracted with DCM. The DCM layer was washed with brine, dried over anhydrous sodium sulfate and evaporated. Purification of the crude product by preparative TLC using methanol/dichloromethane (1:15) mixture as eluent afforded tert-butyl 7-((tert-butoxycarbonyl)amino)-3-(4-carbamoyl-1H-benzo[d]imidazol-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate. MS (ES+): m/z 508.28 [M+H]+

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with DCM
  3. washThe DCM layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customPurification of the crude product by preparative TLC

Sources & evidence

ORD record
ord-0727199c5aaf4fee9d4f2e2bd64a6369
Source dataset
uspto-grants-2013_08
Patent number
US08513433B2

Reaction notes

Loading…