Diisopropylethylamine → HCID 57507377, compound

HRID 556503Notes

Reaction equation

HRID 556503 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]([CH:24]([CH3:26])[CH3:25])[C:5]1([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)[C:13]2[C:8](=[CH:9][C:10]([Br:14])=[CH:11][CH:12]=2)[NH:7][C:6]1=[O:15].CCN(C(C)C)C(C)C.[C:36]([N:39]1[CH2:44][CH2:43][N:42]([C:45](Cl)=[O:46])[CH2:41][CH2:40]1)(=[O:38])[CH3:37]>C(Cl)Cl>[Br:14][C:10]1[CH:9]=[C:8]2[C:13]([C:5]([N:4]([CH:24]([CH3:26])[CH3:25])[CH2:3][CH2:2][NH:1][C:45]([N:42]3[CH2:43][CH2:44][N:39]([C:36](=[O:38])[CH3:37])[CH2:40][CH2:41]3)=[O:46])([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=3)[C:6](=[O:15])[NH:7]2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 13728618HCID 13728618, compoundHCID 57507376HCID 57507376, compound

Product 1

HCID 57507377HCID 57507377, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of rac-3-[(2-Amino-ethyl)-isopropyl-amino]-6-bromo-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one (270 mg, 0.48 mmol) and DIPEA (167 uL, 0.96 mmol) in 5 mL of DCM was added 4-acetyl-piperazine-1-carbonyl chloride (137 mg, 0.72 mmol) at room temperature, and stirred at same temperature overnight. The reaction mixture was rinsed with 20 mL water. The organic layer was dried over Na2SO4, and concentrated in vacuo, then purified by flash column chromatopgraphy to 180 mg white solid. MS: [M+H]+=590.

Workup

  1. washThe reaction mixture was rinsed with 20 mL water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. custompurified by flash column chromatopgraphy to 180 mg white solid

Sources & evidence

ORD record
ord-9e66a45476044b6e825d0c03116888fe
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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