4-Methylmorpholine → Balicatib

HRID 478627Notes

Reaction equation

HRID 478627 reaction equation
[CH2:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.C(N=C=NC(C)C)(C)C.[C:45]([CH2:47][NH:48][C:49]([C:51]1([NH2:57])[CH2:56][CH2:55][CH2:54][CH2:53][CH2:52]1)=[O:50])#[N:46]>C(#N)C.C(O)(=O)C>[C:45]([CH2:47][NH:48][C:49]([C:51]1([NH:57][C:14](=[O:16])[C:13]2[CH:12]=[CH:11][C:10]([N:7]3[CH2:6][CH2:5][N:4]([CH2:1][CH2:2][CH3:3])[CH2:9][CH2:8]3)=[CH:18][CH:17]=2)[CH2:56][CH2:55][CH2:54][CH2:53][CH2:52]1)=[O:50])#[N:46]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 109778124-(4-propylpiperazin-1-yl)benzoic AcidHCID 111946841-Amino-cyclohexanecarboxylic acid cyanomethyl amide

Product 1

HCID 10201696Balicatib

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent2×

Procedure

In an alternative procedure the acetic acid internal salt of 4-[4-(1-propyl)-piperazin-1-yl]-benzoic acid is treated in acetonitrile with HOBt, NMM and diisopropylcarbodiimide (DICI), and after stirring for 1 hr at 40° C. a solution of 1-amino-cyclohexanecarboxylic acid cyanomethyl-amide in acetonitrile is added. On completion of the reaction, the product is precipitated by addition of water to the reaction mixture, filtered and following digestion with ethanol is dried to the end product.

Workup

  1. additionis added
  2. customOn completion of the reaction
  3. customthe product is precipitated by addition of water to the reaction mixture
  4. filtrationfiltered
  5. customis dried to the end product

Sources & evidence

ORD record
ord-a85f5797bfd64b2dbebaae7c30d0554c
Source dataset
uspto-grants-2003_11
Patent number
US06642239B2

Reaction notes

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