Dicyclohexylcarbodiimide → HCID 178523245, compound

HRID 1436962Notes

Reaction equation

HRID 1436962 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]([OH:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:14]([OH:16])=O)=[N:7]2.C1(N=C=NC2CCCCC2)CCCCC1.O.ON1C2C=CC=CC=2N=N1.Cl.Cl.[NH2:45][CH2:46][CH2:47][C:48]1[N:52]=[CH:51][NH:50][CH:49]=1>C(N(CC)CC)C>[NH:50]1[CH:49]=[C:48]([CH2:47][CH2:46][NH:45][C:14]([C:6]2[CH:5]=[CH:4][C:3]3[C:8](=[C:9]([OH:13])[C:10]([Cl:12])=[CH:11][C:2]=3[Cl:1])[N:7]=2)=[O:16])[N:52]=[CH:51]1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 219181905,7-Dichloro-8-hydroxyquinoline-2-carboxylic acidHCID 178478691HCID 178478691, compound

Product 1

HCID 178523245HCID 178523245, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

According to the procedure described in Example 1, 5,7-dichloro-8-hydroxyquinoline-2-carboxylic acid 19 (597 mg, 2.31 mmol), dicyclohexylcarbodiimide (483 mg, 2.31 mmol), 1-hydroxybenzotriazole hydrate (316 mg, 2.31 mmol), histamine dihydrochloride (425 mg, 2.31 mmol) and triethylamine (0.5 mL) gave, after column purification (silica gel, ethyl acetate/isopropanol/water (12:4:1)), 5,7-dichloro-8-hydroxyquinoline-2-carboxylic acid [2-(1H-imidazol-4-yl)-ethyl]-amide (PBT 1038) as a pale straw-coloured solid (276 mg, 34%). 1H NMR (DMSO-d6, 400 MHz): δ 11.40 (br, 2H), 9.74 (m, 1H), 8.64 (d, J=8.6, 1 H), 8.28 (d, J=8.6, 1 H), 7.92 (s, 1H), 7.53 (s, 1H), 6.83 (s, 1H), 3.59 (m, 2H), 2.81 (m, 2H).

Workup

  1. customgave
  2. customafter column purification (silica gel, ethyl acetate/isopropanol/water (12:4:1)), 5,7-dichloro-8-hydroxyquinoline-2-carboxylic acid [2-(1H-imidazol-4-yl)-ethyl]-amide (PBT 1038) as a pale straw-coloured solid (276 mg, 34%)

Sources & evidence

ORD record
ord-25facb826c394e49b5de02cbdc8faa78
Source dataset
uspto-grants-2009_11
Patent number
US07619091B2

Reaction notes

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