1,2-Dichloroethane → HCID 66920289, compound

HRID 1510063Notes

Reaction equation

HRID 1510063 reaction equation
O(C1N(C2C=CC=CC=2)C2C(C=1C(O)=O)=CC=CC=2)C1C=CC=CC=1.[O:26]([C:33]1[N:34]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:35]2[C:40]([C:41]=1[CH:42]=[O:43])=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[N:50]1([C:57]([O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:58])[CH2:56][CH2:55][CH2:54][NH:53][CH2:52][CH2:51]1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.CN1CCOCC1>CN(C=O)C>[C:60]([O:59][C:57]([N:50]1[CH2:56][CH2:55][CH2:54][N:53]([C:42]([C:41]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[N:34]([C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)[C:33]=2[O:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[O:43])[CH2:52][CH2:51]1)=[O:58])([CH3:63])([CH3:61])[CH3:62]

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylateHCID 22097786HCID 22097786, compoundHCID 86651030HCID 86651030, compound

Product 1

HCID 66920289HCID 66920289, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-phenoxy-1-phenyl-1H-indole-3-carboxylic acid (164 mg, 499 μmol; available by oxidation of 2-phenoxy-1-phenyl-1H-indole-3-carbaldehyde (DE 2707268) analogously as described in example 11, step 5), tert-butyl 1-homopiperazinecarboxylate (100 mg, 499 μmol), EDC (105 mg, 549 μmol) and HOAT (78.2 mg, 574 μmol) in DMF (2 ml) was added NMM (165 μl, 1.49 mmol) and the reaction mixture was stirred at room temperature overnight. The mixture was filtered and purified by preparative HPLC. The eluate was lyophilized overnight to give 169 mg of the title compound.

Workup

  1. filtrationThe mixture was filtered
  2. custompurified by preparative HPLC
  3. waitThe eluate was lyophilized overnight

Sources & evidence

ORD record
ord-a133b87209e24b9f97ec30e47081e388
Source dataset
uspto-grants-2012_07
Patent number
US08211885B2

Reaction notes

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