Phenyl isocyanate → 4-[3-(4-N-Phenylcarbamylaminophenyl)-1-ethyl-1H-pyrazol-4-yl]-2-[3-(dimethylaminomethyl)phenyl]-1H-pyrrolo[2,3-b]pyridine

HRID 28886Notes

Reaction equation

HRID 28886 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]4[NH:19][C:20]([C:22]5[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][N:29]([CH3:31])[CH3:30])[CH:23]=5)=[CH:21][C:14]=34)=[CH:11][N:10]([CH2:32][CH3:33])[N:9]=2)=[CH:4][CH:3]=1.[C:34]1([N:40]=[C:41]=[O:42])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>O1CCCC1.CCN(CC)CC>[CH3:33][CH2:32][N:10]1[N:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:41]([NH:40][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[O:42])=[CH:7][CH:6]=2)[C:12]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]3[C:14]=2[CH:21]=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][N:29]([CH3:30])[CH3:31])[CH:23]=2)[NH:19]3)=[CH:11]1

Participants

5

Reactant 2

HCID 7672Phenyl isocyanateHCID 689990183-[4-[3-(4-Aminophenyl)-1-ethyl-1H-pyrazol-4-yl]-1H-pyrrolo[2,3-b]pyridin-2-yl]-N,N-dimethylbenzenemethanamine

Product 1

HCID 248159634-[3-(4-N-Phenylcarbamylaminophenyl)-1-ethyl-1H-pyrazol-4-yl]-2-[3-(dimethylaminomethyl)phenyl]-1H-pyrrolo[2,3-b]pyridineYield 44%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-[3-(4-aminophenyl)-1-ethyl-1H-pyrazol-4-yl]-2-[3-(dimethylaminomethyl)phenyl]-1H-pyrrolo[2,3-b]pyridine (0.34 mmol) in tetrahydrofuran (5 mL) was added phenyl isocyanate (0.41 mmol) and two drops of Et3N. The reaction was stirred at room temperature for 1 h and concentrated to dryness under vacuum. The remaining solid was triturated with (1:1) diethyl ether:petroleum ether, filtered, and dried under vacuum. Purification by Gilson reverse phase HPLC gave the title compound as an off-white solid (44%). ESMS (M+H)+: 556.4

Workup

  1. concentrationconcentrated to dryness under vacuum
  2. customThe remaining solid was triturated with (1:1) diethyl ether
  3. filtrationpetroleum ether, filtered
  4. customdried under vacuum
  5. customPurification by Gilson reverse phase HPLC

Sources & evidence

ORD record
ord-b58263bf4b944d1bbba33c65eb648272
Source dataset
uspto-grants-2008_09
Patent number
US07419988B2

Reaction notes

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