Hydrochloric Acid → HCID 11340914, compound

HRID 1297184Notes

Reaction equation

HRID 1297184 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]2[S:11][C:12]([C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[CH3:23])=[O:16])=[CH:13][N:14]=2)[CH:6]=[CH:7][CH:8]=1.Cl.[F:25][C:26]1[CH:27]=[CH:28][C:29]([CH3:36])=[C:30]([S:32](Cl)(=[O:34])=[O:33])[CH:31]=1.CCN(CC)CC>C(Cl)Cl>[F:25][C:26]1[CH:27]=[CH:28][C:29]([CH3:36])=[C:30]([S:32]([NH:1][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[C:5]([NH:9][C:10]3[S:11][C:12]([C:15](=[O:16])[C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[CH3:23])=[CH:13][N:14]=3)[CH:4]=2)(=[O:34])=[O:33])[CH:31]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 1362865-Fluoro-2-methylbenzenesulphonyl chlorideHCID 58914623HCID 58914623, compound

Product 1

HCID 11340914HCID 11340914, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 35.8 mg (0.1 mmol)[2-(3-aminomethyl-phenylamino)-thiazol-5-yl]-o-tolyl-methanone; hydrochloride, 25 mg (0.12 mmol) 5-fluoro-2-methyl-benzenesulfonyl chloride (commercially available) and 69 ul (0.5 mmol) NEt3 in 3 ml DCM was stirred at 60° C. for 16 h. After evaporation of the volatiles the residue was taken up in 1.5 ml MeOH/formic acid 2/1 and subjected to reversed phase HPLC purification eluting with a gradient of acetonitrile/water. After evaporation of the product fractions 31 mg (62%) of the title compound was obtained.

Workup

  1. customAfter evaporation of the volatiles the residue
  2. customsubjected to reversed phase HPLC purification
  3. washeluting with a gradient of acetonitrile/water
  4. customAfter evaporation of the product fractions 31 mg (62%) of the title compound
  5. customwas obtained

Sources & evidence

ORD record
ord-149bfd12084e49558fa52d103f0732b7
Source dataset
uspto-grants-2007_07
Patent number
US07250431B2

Reaction notes

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