Benzyl isocyanate → HCID 10119278, compound

HRID 970917Notes

Reaction equation

HRID 970917 reaction equation
[NH2:1][CH2:2][C:3]1[CH:30]=[CH:29][C:6]([CH2:7][N:8]([CH2:19][C:20]2[NH:24][C:23]3[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=3[N:21]=2)[CH:9]2[C:18]3[N:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[CH2:31]([N:38]=[C:39]=[O:40])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(Cl)Cl>[NH:24]1[C:23]2[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=2[N:21]=[C:20]1[CH2:19][N:8]([CH2:7][C:6]1[CH:5]=[CH:4][C:3]([CH2:2][NH:1][C:39]([NH:38][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:40])=[CH:30][CH:29]=1)[CH:9]1[C:18]2[N:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 76639Benzyl isocyanateHCID 21985008N-[(1H-Benzo[d]imidazol-2-yl)methyl]-N-(4-(aminomethyl)-benzyl)-5,6,7,8-tetrahydroquinolin-8-amine

Product 1

HCID 10119278HCID 10119278, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (0° C.) solution of (4-aminomethyl-benzyl)-(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (0.130 g, 0.33 mmol) in CH2Cl2 (3.5 mL) was added benzyl isocyanate (45 μL, 0.36 mmol) and the resultant solution was stirred for 100 minutes. The cooling bath was removed and the mixture was concentrated under reduced pressure. Purification of the crude material by column chromatography on silica gel (25:1:1 CH2Cl2—CH3OH—NH4OH) followed by radial chromatography on silica gel (1 mm plate, 25:1:1 CH2Cl2—CH3OH—NH4OH) provided the free base of the title compound (0.047 g, 28%) as a white solid.

Workup

  1. customThe cooling bath was removed
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customPurification of the crude material by column chromatography on silica gel (25:1:1 CH2Cl2—CH3OH—NH4OH)

Sources & evidence

ORD record
ord-229cf74d4fd14d4ba7ad0209b2067204
Source dataset
uspto-grants-2007_12
Patent number
US07312234B2

Reaction notes

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