1,2-Dichloroethane → n-[4-({[2-(2,4-Dichlorophenoxy)phenyl]amino}sulfonyl)phenyl]pyrimidine-5-carboxamide

HRID 746745Notes

Reaction equation

HRID 746745 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=2[Cl:26])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[N:27]1[CH:32]=[C:31]([C:33](O)=[O:34])[CH:30]=[N:29][CH:28]=1.C(Cl)CCl.C(N(CC)CC)C.FC(F)(F)C(O)=O>CN(C=O)C.COCCOC>[Cl:26][C:20]1[CH:21]=[C:22]([Cl:25])[CH:23]=[CH:24][C:19]=1[O:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[NH:11][S:8]([C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:33]([C:31]2[CH:32]=[N:27][CH:28]=[N:29][CH:30]=2)=[O:34])=[CH:7][CH:6]=1)(=[O:9])=[O:10]

Participants

8

Reactant 5

HCID 111,2-Dichloroethane2×HCID 6422Trifluoroacetic acidHCID 8471Triethylamine2×HCID 78346Pyrimidine-5-carboxylic acid2×HCID 27307034-amino-N-[2-(2,4-dichlorophenoxy)phenyl]benzenesulfonamide

Product 1

HCID 58664940n-[4-({[2-(2,4-Dichlorophenoxy)phenyl]amino}sulfonyl)phenyl]pyrimidine-5-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of the compound of Step 2 (0.1 g, 0.244 mmol), pyrimidin-5-carboxylic acid (0.03 g, 0.244 mmol) HOAT (0.033 g, 0.244 mmol) and EDC (0.047 g, 0.244 mmol) in DMF (1 mL) at room temperature was added triethylamine (0.068 mL, 0.489 mmol). After 18 hr pyrimidin-5-carboxylic acid (0.03 g, 0.244 mmol) HOAT (0.033 g, 0.244 mmol), EDC (0.047 g, 0.244 mmol) and triethylamine (0.068 mL, 0.489 mmol) were added. The reaction mixture was stirred for a further 16 hr, diluted with DME (2 mL), treated with trifluoroacetic acid, and purified directly by reverse phase HPLC waters Prepak C-18 column eluting with 5-95% CH3CN: water containing 0.1% TPA. The pure fractions were combined and lyophilized to afford the title compound. C23H16Cl2N4O4S MH+ requires 515.0342 found 515.0349. Proton NMR (400 MHz, CDCl3) δ 6.53 (d, J=8.8 Hz, 1H), 6.62 (d, J=8.2 Hz), 7.00-7.10 (m, 3H), 7.14 (t, J=7.8 Hz, 1H), 7.41 (d, J=2.5 Hz, 1H), 7.64(d, J=8.6 Hz, 2H), 7.70-7.80 (m, 3H), 8.03(s, 1H), 9.28 (s, 2H), 9.43 (s, 1H).

Workup

  1. custompurified directly by reverse phase HPLC waters Prepak C-18 column
  2. washeluting with 5-95% CH3CN

Sources & evidence

ORD record
ord-c1343ec605e246f39f5da1e18a8a856a
Source dataset
uspto-grants-2008_07
Patent number
US07393873B2

Reaction notes

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