Water → HCID 22502205, compound

HRID 1633987Notes

Reaction equation

HRID 1633987 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([NH:11][C:12](=[O:35])[N:13]([CH2:25][C:26]2[CH:34]=[CH:33][C:29]([C:30](O)=[O:31])=[CH:28][CH:27]=2)[CH:14]2[CH2:19][CH2:18][C:17]3([CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[CH2:16][CH2:15]2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].Cl.CN(C)CCCN=C=NCC.[NH2:48][C:49]1[NH:53][N:52]=[N:51][N:50]=1.O>CN(C=O)C>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([NH:11][C:12](=[O:35])[N:13]([CH2:25][C:26]2[CH:27]=[CH:28][C:29]([C:30]([NH:48][C:49]3[N:50]=[N:51][NH:52][N:53]=3)=[O:31])=[CH:33][CH:34]=2)[CH:14]2[CH2:15][CH2:16][C:17]3([CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[CH2:18][CH2:19]2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22501785HCID 22501785, compoundHCID 178509299HCID 178509299, compound

Product 1

HCID 22502205HCID 22502205, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

4-[3-(3-Methylsulfonylphenyl)-1-spiro[5.5]undec-3-yl-ureidomethyl]benzoic acid (32.2 mg, 64.6 μmol) was dissolved in DMF (1 mL) and added N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (EDAC) (16.5 mg, 86 μmol) and 5-aminotetrazole.H2O (16,5 mg, 160 μmol). The mixture was stirred at 25° C. for 1 day and concentrated in vacuo. Brine (5 mL) was added to the residue followed by a mixture of ethanol and chloroform (1:2, 10 mL). The phases were separated and the aqueous layer was extracted with a mixture of ethanol and chloroform (1:2, 2×10 mL). The combined organic extracts were dried over MgSO4 and evaporated. The residue was purified by preparative HPLC affording the title compound.

Workup

  1. concentrationconcentrated in vacuo
  2. additionBrine (5 mL) was added to the residue
  3. additionfollowed by a mixture of ethanol and chloroform (1:2, 10 mL)
  4. customThe phases were separated
  5. extractionthe aqueous layer was extracted with a mixture of ethanol and chloroform (1:2, 2×10 mL)
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. customevaporated
  8. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-5f8b1bbd46b84a1a97098318fe177b99
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

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