Triethylamine → N-{4-[6-(3-Chloro-benzoyl)-6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3',4'-d]pyrrol-4-ylamino]-phenyl}-benzamide

HRID 533731Notes

Reaction equation

HRID 533731 reaction equation
[N:1]1[C:6]2[NH:7][C:8]3[CH2:13][CH2:12][NH:11][CH2:10][C:9]=3[C:5]=2[C:4]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:29])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:17][CH:16]=2)=[CH:3][CH:2]=1.[Cl:30][C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][CH:39]=1)[C:34](Cl)=[O:35].C(N(CC)CC)C>ClCCCl>[Cl:30][C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][CH:39]=1)[C:34]([N:11]1[CH2:12][CH2:13][C:8]2[NH:7][C:6]3[N:1]=[CH:2][CH:3]=[C:4]([NH:14][C:15]4[CH:16]=[CH:17][C:18]([NH:21][C:22](=[O:29])[C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=5)=[CH:19][CH:20]=4)[C:5]=3[C:9]=2[CH2:10]1)=[O:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69252Benzoyl chloride, 3-chloro-HCID 46843080N-[4-(6,7,8,9-Tetrahydro-5H-dipyrido[2,3-b;3',4'-d]pyrrol-4-ylamino)-phenyl]-benzamide

Product 1

HCID 46843213N-{4-[6-(3-Chloro-benzoyl)-6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3',4'-d]pyrrol-4-ylamino]-phenyl}-benzamideYield 49.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

N-[4-(6,7,8,9-Tetrahydro-5H-dipyrido[2,3-b;3′,4′-d]pyrrol-4-ylamino)-phenyl]-benzamide (40 mg, 0.1 mmol), 3-chlorobenzoyl chloride (22 mg, 0.13 mmol), and triethylamine (0.04 mL, 0.31 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 12 (26 mg, 48% yield) as a brown solid. LC-MS (M+H=522, obsd.=522).

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-be27b951c8174c97b1971fd1af25ca21
Source dataset
uspto-grants-2014_10
Patent number
US08853391B2

Reaction notes

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