1,2-Dichloroethane → HCID 57678519, compound

HRID 491681Notes

Reaction equation

HRID 491681 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11]([C:13]2[CH:18]=[C:17]([O:19][C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([NH2:27])[CH:21]=3)[CH:16]=[CH:15][N:14]=2)=[O:12])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([N:35]=[C:36]=S)=[CH:31][CH:30]=1.CC#N.C(Cl)CCl>CC#N.CN(C=O)C>[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11]([C:13]2[CH:18]=[C:17]([O:19][C:20]3[CH:25]=[CH:24][C:23]4[O:26][C:36]([NH:35][C:32]5[CH:33]=[CH:34][C:29]([Cl:28])=[CH:30][CH:31]=5)=[N:27][C:22]=4[CH:21]=3)[CH:16]=[CH:15][N:14]=2)=[O:12])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 6342AcetonitrileHCID 164804-Chlorophenyl isothiocyanateHCID 86760863HCID 86760863, compound

Product 1

HCID 57678519HCID 57678519, compound

Reagents, catalysts & solvents 1

HCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

4-(3-Amino-4-hydroxy-phenoxy)-pyridine-2-carboxylic acid (4-pyrrolidin-1-yl-butyl)-amide (Example 253, Step E, 165 mg, 0.4 mmol, 1.0 eq.) was dissolved in CH3CN/DMF (2/1, v/v, 15 ml) and 1-chloro-4-isothiocyanato-benzene (as described in preparation III, 75 mg, 0.4 mmol, 1.0 eq.) in as a CH3CN solution was added dropwise. The reaction was stirred at RT for 16 h. EDC (85 mg, 0.4 mmol, 1.0 eq.) was added and the reaction was heated to 80° C. for 2 h. The mixture was concentrated and the crude product was purified by column chromatography (0-10% MeOH/CH2Cl2/1% NH4OH) to yield 4-[2-(4-chloro-phenylamino)-benzoxazol-5-yloxy]-pyridine-2-carboxylic acid (4-pyrrolidin-1-yl-butyl)-amide. MS m/z=506.01 (M+H)+Calc'd for C27H28ClN5O3: 505.19.

Workup

  1. temperaturethe reaction was heated to 80° C. for 2 h
  2. concentrationThe mixture was concentrated
  3. customthe crude product was purified by column chromatography (0-10% MeOH/CH2Cl2/1% NH4OH)

Sources & evidence

ORD record
ord-c267470534be463e9d07d888be17d59b
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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