Triethylamine → 4-Phenylamino-5,7,8,9-tetrahydro-dipyrido[2,3-b;3',4'-d]pyrrole-6-carboxylic acid (3-chloro-phenyl)-amide

HRID 533729Notes

Reaction equation

HRID 533729 reaction equation
[C:1]1([NH:7][C:8]2[C:16]3[C:15]4[CH2:17][NH:18][CH2:19][CH2:20][C:14]=4[NH:13][C:12]=3[N:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:21][C:22]1[CH:23]=[C:24]([N:28]=[C:29]=[O:30])[CH:25]=[CH:26][CH:27]=1.C(N(CC)CC)C>ClCCCl>[Cl:21][C:22]1[CH:23]=[C:24]([NH:28][C:29]([N:18]2[CH2:19][CH2:20][C:14]3[NH:13][C:12]4[N:11]=[CH:10][CH:9]=[C:8]([NH:7][C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)[C:16]=4[C:15]=3[CH2:17]2)=[O:30])[CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 17968Benzene, 1-chloro-3-isocyanato-HCID 46843082Phenyl-(6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3',4'-d]pyrrol-4-yl)-amine

Product 1

HCID 468431464-Phenylamino-5,7,8,9-tetrahydro-dipyrido[2,3-b;3',4'-d]pyrrole-6-carboxylic acid (3-chloro-phenyl)-amideYield 25.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Phenyl-(6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3′,4′-d]pyrrol-4-yl)-amine (40 mg, 0.15 mmol), 3-chlorophenyl isocyanate (28 mg, 0.18 mmol), and triethylamine (0.06 mL, 0.45 mmol) were dissolved in 1,2-dichloroethane (2.0 mL), and stirred overnight at room temperature. The reaction mixture was added directly to a Biotage column. The crude product was purified via Biotage eluting with CH2Cl2/MeOH (9/1, v/v) to provide 10 (16 mg, 25% yield) as an off-white solid. LC-MS (M+H=418, obsd.=418).

Workup

  1. additionThe reaction mixture was added directly to a Biotage column
  2. customThe crude product was purified via Biotage
  3. washeluting with CH2Cl2/MeOH (9/1

Sources & evidence

ORD record
ord-d12a63cd563a4d89ac591c56c8490083
Source dataset
uspto-grants-2014_10
Patent number
US08853391B2

Reaction notes

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