1-Hydroxybenzotriazole → HCID 136348817, compound

HRID 1180534Notes

Reaction equation

HRID 1180534 reaction equation
O=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[N:12]=[C:13]([C:22](O)=[O:23])[NH:14][C:15]=3[C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[OH:25][N:26]1C2C=CC=CC=2N=N1.[N:35]1([CH2:41][CH2:42][NH2:43])[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1>CN(C=O)C.ClCCl>[N:35]1([CH2:41][CH2:42][NH:43][C:22]([C:13]2[NH:14][C:15]([C:16]3[CH:17]=[CH:18][N:19]=[CH:20][CH:21]=3)=[C:11]([C:7]3[CH:6]=[C:5]4[C:10](=[CH:9][CH:8]=3)[C:2](=[N:26][OH:25])[CH2:3][CH2:4]4)[N:12]=2)=[O:23])[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1

Participants

6

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 4082852-MorpholinoethylamineHCID 17953828HCID 17953828, compound

Product 1

HCID 136348817HCID 136348817, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of the product of Description 1 (105 mg, 0.33 mmol), 1-hydroxybenzotriazole (68 mg, 0.5 mmol) and N-cyclohexylcarbodiimide-N′-methyl polystyrene (500 mg, 0.66 mmol, resin loading 1.32 mmol/g) in DMF (2 ml) was stirred at room temperature for 30 minutes. A solution of 2-morpholin-4-yl-ethylamine (43 mg, 0.33 mmol) in dichloromethane (0.5 ml) was added and the mixture stirred at room temperature for 24 hours. The mixture was filtered through an SCX cation exchange resin column eluting with methanol followed by 10% 0.880 ammonia solution in methanol to elute the product. Following concentration, the residue was purified by silica gel chromatography eluting with a 1:9:90 mixture of 0.880 ammonia solution: methanol:chloroform gave the title compound (65 mg, 46%) as a yellow solid; MS(AP+) m/e 432 [M+H]+.

Workup

  1. stirringthe mixture stirred at room temperature for 24 hours
  2. filtrationThe mixture was filtered through an SCX cation exchange resin column
  3. washeluting with methanol
  4. washto elute the product
  5. concentrationconcentration
  6. customthe residue was purified by silica gel chromatography
  7. washeluting with a 1:9:90 mixture of 0.880 ammonia solution

Sources & evidence

ORD record
ord-7f3390a24f8540268843758d56a3b61e
Source dataset
uspto-grants-2007_10
Patent number
US07282500B2

Reaction notes

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