Chloroform → N3-(4-methoxybenzoyl)-N4-[4-methoxy-2-[3-(1-methylpyrrol-2-ylcarbonyl)aminopropoxy]benzoyl]-3,4-pyridinediamine

HRID 1445445Notes

Reaction equation

HRID 1445445 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([OH:9])=O.C(Cl)(Cl)Cl.N=C=N.[CH3:17][O:18][C:19]1[CH:49]=[CH:48][C:22]([C:23]([NH:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][C:31]=2[NH:32][C:33](=[O:47])[C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][C:35]=2[O:42][CH2:43][CH2:44][CH2:45][NH2:46])=[O:24])=[CH:21][CH:20]=1>CC=C(C)C>[CH3:17][O:18][C:19]1[CH:20]=[CH:21][C:22]([C:23]([NH:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][C:31]=2[NH:32][C:33](=[O:47])[C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][C:35]=2[O:42][CH2:43][CH2:44][CH2:45][NH:46][C:7]([C:3]2[N:2]([CH3:1])[CH:6]=[CH:5][CH:4]=2)=[O:9])=[O:24])=[CH:48][CH:49]=1

Participants

6

Reactant 4

HCID 6212Chloroform2×HCID 814531-Methyl-2-pyrrolecarboxylic acidHCID 160435CarbodiimideHCID 69491278N3-(4-methoxybenzoyl)-N4-[4-methoxy-2-(3-aminopropoxy)benzoyl]-3,4-pyridinediamine

Product 1

HCID 11563084N3-(4-methoxybenzoyl)-N4-[4-methoxy-2-[3-(1-methylpyrrol-2-ylcarbonyl)aminopropoxy]benzoyl]-3,4-pyridinediamineYield 27%

Reagents, catalysts & solvents 1

HCID 105532-Methyl-2-buteneSolvent2×

Procedure

1-Methyl-2-pyrrolecarboxylic acid (57.6 mg, 460 μmol) was dissolved in amylene stabilized chloroform (8 mL). Resin-supported carbodiimide (1.1 g, 0.85 mm ol/g, 920 μmol) was added. To the resin-acid slurry was added N3-(4-methoxybenzoyl)-N4-[4-methoxy-2-(3-aminopropoxy)benzoyl]-3,4-pyridinediamine (106 mg crude, 230 μmol) in amylene stabilized chloroform (5 mL). The vial was capped and the reaction was agitated overnight on an orbital platform shaker. The slurry was filtered. The filtrate was concentrated and then purified by semipreparative HPLC as described in Example 2-F to provide N3-(4-methoxybenzoyl)-N4-[4-methoxy-2-[3-(1-methylpyrrol-2-ylcarbonyl)aminopropoxy]benzoyl]-3,4-pyridinediamine (17.3 mg, 27%) as ivory needles.

Workup

  1. customThe vial was capped
  2. filtrationThe slurry was filtered
  3. concentrationThe filtrate was concentrated
  4. custompurified by semipreparative HPLC

Sources & evidence

ORD record
ord-99d5340f4c93460081fc82a28eeec5fc
Source dataset
uspto-grants-2010_02
Patent number
US07666866B2

Reaction notes

Loading…