Water → HCID 58247405, compound

HRID 2359657Notes

Reaction equation

HRID 2359657 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]=[C:9]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)[N:8]=2)=[CH:4][CH:3]=1.CCN(CC)CC.[CH:31]1([C:34](Cl)=[O:35])[CH2:33][CH2:32]1.O>C(Cl)Cl>[CH:31]1([C:34]([NH:1][C:2]2[CH:23]=[CH:22][C:5]([O:6][C:7]3[C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]=[C:9]([C:16]4[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=4)[N:8]=3)=[CH:4][CH:3]=2)=[O:35])[CH2:33][CH2:32]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 58247412HCID 58247412, compound

Product 1

HCID 58247405HCID 58247405, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Compound 17c (0.5 g; 1.6 mmol) in CH2Cl2 (6 mL) was added Et3N (0.72 mL; 6.4 mmol) and cyclopropylcarbonyl chloride (0.19 mL; 2.1 mmol). The solution was stirred at room temperature for 1 h, then poured the reaction mixture into water. Filtered to collect the solid and dried to afford Compound 17d (410 mg; 68% yield). MS: m/z 376.1 (M+H)+.

Workup

  1. filtrationFiltered
  2. customto collect the solid
  3. customdried

Sources & evidence

ORD record
ord-2efc9df21a4947a29540a99e799ee5c3
Source dataset
uspto-grants-2014_04
Patent number
US08685990B2

Reaction notes

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