Dichloromethane → 5-(4-tert-butylthiazol-2-ylamino)-N-(thiazol-2-yl)pyridine-2-sulfonamide
Reaction equation
FC(F)(F)C(O)=O.COC1C=C(OC)C=CC=1C[N:13]([C:33]1[S:34][CH:35]=[CH:36][N:37]=1)[S:14]([C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]2[S:25][CH:26]=[C:27]([C:29]([CH3:32])([CH3:31])[CH3:30])[N:28]=2)=[CH:19][N:18]=1)(=[O:16])=[O:15].C(Cl)Cl>>[C:29]([C:27]1[N:28]=[C:24]([NH:23][C:20]2[CH:21]=[CH:22][C:17]([S:14]([NH:13][C:33]3[S:34][CH:35]=[CH:36][N:37]=3)(=[O:16])=[O:15])=[N:18][CH:19]=2)[S:25][CH:26]=1)([CH3:32])([CH3:30])[CH3:31]Participants
4
Procedure
Trifluoroacetic Acid (49.4 uL, 0.641 mmol) was added to a solution of 5-(4-tert-Butyl-thiazol-2-ylamino)-pyridine-2-sulfonic acid (2,4-dimethoxy-benzyl)-thiazol-2-yl-amide (35 mg, 0.064 mmol) in Methylene chloride (0.39 mL, 6.1 mmol). After 30 min, the reaction mixture was concentrated in vacuo. The residue was dissolved in DMSO and purified on Gilson (semi-prep, reverse phase, Phenomenex 100×21.2 mm 10 micron C18 column, 20 mL/min, Gradient 85% A to 100% B over 25 min. Solvent A: 7800 water/200 acetonitrile/8 TFA. Solvent B: 7200 acetonitrile/800 water/8 TFA). Fractions were checked by LC/MS and then dried on a lyophilizer to give the desired product as a pale yellow powder.
Workup
- concentrationthe reaction mixture was concentrated in vacuo
- dissolutionThe residue was dissolved in DMSO
- custompurified on Gilson (semi-prep, reverse phase, Phenomenex 100×21.2 mm 10 micron C18 column, 20 mL/min, Gradient 85% A to 100% B over 25 min. Solvent A: 7800 water/200 acetonitrile/8 TFA. Solvent B: 7200 acetonitrile/800 water/8 TFA)
- customdried on a lyophilizer
Sources & evidence
- ORD record
- ord-e7599568f39540dbbb5474cda2471b66
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08124610B2
Reaction notes
Loading…