2,2-Dimethylbutyryl chloride → HCID 71234016, compound

HRID 710017Notes

Reaction equation

HRID 710017 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][NH:5][C:6]([C:8]1[CH:9]=[CH:10][C:11]([N:22]2[CH2:27][CH2:26][N:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:34])[CH2:24][CH2:23]2)=[C:12]([NH:14][C:15]([C:17]2[O:18][CH:19]=[CH:20][CH:21]=2)=[O:16])[CH:13]=1)=[O:7].C(N(C(C)C)CC)(C)C.[CH3:44][C:45]([CH3:51])([CH2:49][CH3:50])[C:46](Cl)=[O:47]>C(Cl)Cl>[CH3:44][C:45]([CH3:51])([CH2:49][CH3:50])[C:46]([N:2]([CH3:1])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[CH:9]=[CH:10][C:11]([N:22]2[CH2:23][CH2:24][N:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:34])[CH2:26][CH2:27]2)=[C:12]([NH:14][C:15]([C:17]2[O:18][CH:19]=[CH:20][CH:21]=2)=[O:16])[CH:13]=1)=[O:7])=[O:47]

Participants

5

Reactant 3

HCID 799582,2-Dimethylbutyryl chlorideHCID 81531DiisopropylethylamineHCID 71234014HCID 71234014, compound

Product 1

HCID 71234016HCID 71234016, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
12.5 °C

Procedure

Furan-2-carboxylic acid [5-{2-[(2,2-dimethyl-butyryl)-methyl-amino]-ethylcarbamoyl}-2-(4-o-tolyl-piperazin-1-yl)-phenyl]-amide (compound no. 133) was prepared as follows: To a solution of furan-2-carboxylic acid [5-(2-methylamino-ethylcarbamoyl)-2-(4-o-tolyl-piperazin-1-yl)-phenyl]-amide (0.04 g, 0.086 mmol) and diisopropylethylamine (0.5 mL) in CH2Cl2 (2.0 mL), 2,2-dimethyl butyryl chloride (0.173 mmol) was added at 0° C., and the reaction was stirred at 0-25° C. for 4 h. Reaction was diluted with CH2Cl2 and washed with a solution of saturated NaHCO3. Organic layer was concentrated and dissolved in ACN and purified on preparative HPLC using water/MeOH (0.1% TFA) as eluent to give the product (0.01 g, 21% yield).

Workup

  1. customReaction
  2. washwashed with a solution of saturated NaHCO3
  3. concentrationOrganic layer was concentrated
  4. dissolutiondissolved in ACN
  5. custompurified on preparative HPLC

Sources & evidence

ORD record
ord-e0fc392b2a7b449898408c3f3dc0ade6
Source dataset
uspto-grants-2015_11
Patent number
US09181226B2

Reaction notes

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