HCID 66889465, compound → HCID 49854331, compound

HRID 1895548Notes

Reaction equation

HRID 1895548 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[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16][N:15]1[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])=O>C(O)(=O)C>[C:8]([C:7]1[C:2]2[N:1]=[C:12]([CH:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:17][CH2:16][N:15]3[C:24]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])[NH:11][C:3]=2[CH:4]=[CH:5][CH:6]=1)(=[O:10])[NH2:9]

Participants

3

Reactant 1

HCID 66889465HCID 66889465, compound

Product 1

HCID 49854331HCID 49854331, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Step-2: A solution of benzyl 1-((2-amino-3-carbamoylphenyl)carbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (425 mg, 0.956 mmol) in acetic acid (5 ml) was heated to 80° C. and stirred overnight. 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 over silica gel column using ethyl acetate/hexane mixture (1:1) as eluent afforded benzyl 1-(4-carbamoyl-1H-benzo[d]imidazol-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate. MS (ES+): m/z 427.2 [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 over silica gel column

Sources & evidence

ORD record
ord-f4fe45a302064e5bbc24b209af664550
Source dataset
uspto-grants-2013_08
Patent number
US08513433B2

Reaction notes

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