Hydrochloric Acid → HCID 86612151, compound

HRID 1867983Notes

Reaction equation

HRID 1867983 reaction equation
[CH:1]1([C:4]([NH:6][C:7]2[S:8][C:9]3[CH:15]=[C:14]([O:16][S:17]([C:20]4[CH:25]=[CH:24][C:23](F)=[CH:22][CH:21]=4)(=[O:19])=[O:18])[CH:13]=[CH:12][C:10]=3[N:11]=2)=[O:5])[CH2:3][CH2:2]1.[CH:27]([NH:30][CH2:31][CH2:32][NH2:33])([CH3:29])[CH3:28].[ClH:34]>CN1C(=O)CCC1.CCOC(C)=O>[ClH:34].[CH:1]1([C:4]([NH:6][C:7]2[S:8][C:9]3[CH:15]=[C:14]([O:16][S:17]([C:20]4[CH:25]=[CH:24][C:23]([NH:33][CH2:32][CH2:31][NH:30][CH:27]([CH3:29])[CH3:28])=[CH:22][CH:21]=4)(=[O:19])=[O:18])[CH:13]=[CH:12][C:10]=3[N:11]=2)=[O:5])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 88098N-IsopropylethylenediamineHCID 115239994-Fluorobenzenesulfonic acid 2-(cyclopropanecarbonylamino)-benzothiazol-6-yl ester

Product 1

HCID 86612151HCID 86612151, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent3×HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 4-fluorobenzenesulfonic 2-(cyclopropanecarbonylamino)benzo-thiazol-6-yl ester (example 53, brevetbenzothiazole_V2) (145 mg, 0.37 mmol) and N-isopropylethylenediamine (233 μl, 1.85 mmol) in 4.5 ml of NMP is heated at 150° C. by microwave for 5 minutes. The crude reaction product is diluted with EtOAc, washed 3 times with water and extracted twice with EtOAc. The organic phases are combined, dried over sodium sulfate, filtered and then evaporated to dryness. The 165 mg of crude product are purified by chromatography on silica: 8 g AIT column, eluent: 90/10/1 CH2Cl2/MeOH/—NH4OH. The solid obtained (96 mg) is dissolved in EtOAc and then brought to pH 2 with hydrochloric acid dissolved in EtOAc. The suspension is evaporated to dryness and taken up in 5 ml of water, and then freeze-dried to give 76 mg of 4-(2-isopropylaminoethylamino)benzenesulfonic 2-(cyclo-propanecarbonylamino)benzothiazol-6-yl ester hydrochloride.

Workup

  1. customThe crude reaction product
  2. washwashed 3 times with water
  3. extractionextracted twice with EtOAc
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe 165 mg of crude product are purified by chromatography on silica
  8. customThe solid obtained (96 mg)
  9. customThe suspension is evaporated to dryness
  10. customfreeze-dried

Sources & evidence

ORD record
ord-e403c2a03b9a4c96bbe9567124594fbb
Source dataset
uspto-grants-2009_12
Patent number
US07632952B2

Reaction notes

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