Pyridine → 5-[(2-Adamantan-1-ylmethyl-5-phenyl-1H-pyrrole-3-carbonyl)-amino]-isophthalic Acid Dibenzyl Ester

HRID 1018302Notes

Reaction equation

HRID 1018302 reaction equation
[C:1]12([CH2:11][C:12]3[NH:13][C:14]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:15][C:16]=3[C:17](O)=[O:18])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.S(Cl)(Cl)=O.[CH2:30]([O:37][C:38](=[O:56])[C:39]1[CH:54]=[C:53]([NH2:55])[CH:52]=[C:41]([C:42]([O:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[O:43])[CH:40]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.N1C=CC=CC=1>C(Cl)Cl.CN(C=O)C>[CH2:45]([O:44][C:42](=[O:43])[C:41]1[CH:52]=[C:53]([NH:55][C:17]([C:16]2[CH:15]=[C:14]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[NH:13][C:12]=2[CH2:11][C:1]23[CH2:10][CH:5]4[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]4)[CH2:2]2)[CH2:8]3)=[O:18])[CH:54]=[C:39]([C:38]([O:37][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:56])[CH:40]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 7023592Dibenzyl 5-aminoisophthalateHCID 113820842-Adamantan-1-ylmethyl-5-phenyl-1h-pyrrole-3-carboxylic acid

Product 1

HCID 112393395-[(2-Adamantan-1-ylmethyl-5-phenyl-1H-pyrrole-3-carbonyl)-amino]-isophthalic Acid Dibenzyl EsterYield 45%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of the product of step c above (290 mg, 0.91 mmol) in DCM (5 ml) was added thionyl chloride (200 μl, 2.74 mmol) and one drop of DMF. The mixture was stirred at room temperature for 30 min, the solvent was evaporated and the residue was coevaporated with DCM (2×5 ml). 5-Amino-isophthalic acid dibenzyl ester (361 mg, 1.00 mmol) was added to the residue followed by anhydrous pyridine (2 ml). The solution was kept at room temperature for 16 h and diluted with DCM (30 ml). The organic phase was washed with 2M hydrochloric acid (2×20 ml), brine (20 ml), dried (MgSO4) and the solvent was evaporated. The residue was purified by flash column chromatography (silica, DCM/hexane/ethyl acetate 9:9:2) to afford the product as pale yellow solid (300 mg, 45%). 1H NMR (300 MHz, CDCl3) 8.48 (3H, s), 8.30 (1H, br s), 7.69 (1H, s), 7.49-7.27 (15H, m), 6.66 (1H, d), 5.40 (4H, s), 2.91 (2H, s), 1.95 (3H, br s), 1.63 (12H, m).

Workup

  1. customthe solvent was evaporated
  2. waitThe solution was kept at room temperature for 16 h
  3. washThe organic phase was washed with 2M hydrochloric acid (2×20 ml), brine (20 ml)
  4. dry with materialdried (MgSO4)
  5. customthe solvent was evaporated
  6. customThe residue was purified by flash column chromatography (silica, DCM/hexane/ethyl acetate 9:9:2)

Sources & evidence

ORD record
ord-d9848bcf4cc345ffad797f0a446ee384
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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