Benzoyl isocyanate → HCID 117667367, compound

HRID 712665Notes

Reaction equation

HRID 712665 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:16]=[C:17]3[C:22](=[N:23][CH:24]=2)[NH:21][CH2:20][CH2:19][CH2:18]3)[CH:12]=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]([N:33]=[C:34]=[O:35])(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:16]=[C:17]3[C:22](=[N:23][CH:24]=2)[N:21]([C:34]([NH:33][C:25](=[O:32])[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[O:35])[CH2:20][CH2:19][CH2:18]3)[CH:12]=[N:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 78210Benzoyl isocyanateHCID 117667100HCID 117667100, compound

Product 1

HCID 117667367HCID 117667367, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(5-benzyloxy-pyridin-3-yl)-1,2,3,4-tetrahydro-[1,8]naphthyridine (530 mg, 1.7 mmol) in DCM (18 mL) is added benzoyl isocyanate (368 mg, 2.5 mmol). The resultant mixture is heated at reflux for 2 h. The solvent is removed under vacuum to obtain N-[6-(5-benzyloxy-pyridin-3-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carbonyl]-benzamide (620 mg).

Workup

  1. temperatureat reflux for 2 h
  2. customThe solvent is removed under vacuum

Sources & evidence

ORD record
ord-536b5b3f8fb24f209b995243a4975546
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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