Dichloromethane → 5-(4-tert-butylthiazol-2-ylamino)-N-(thiazol-2-yl)pyridine-2-sulfonamide

HRID 1644666노트

반응식

HRID 1644666 반응식
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]

참가 물질

4

반응물 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 575512625-(4-tert-butylthiazol-2-ylamino)-N-(2,4-dimethoxybenzyl)-N-(thiazol-2-yl)pyridine-2-sulfonamide

생성물 1

HCID 575511755-(4-tert-butylthiazol-2-ylamino)-N-(thiazol-2-yl)pyridine-2-sulfonamide

실험 절차

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.

후처리

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in DMSO
  3. 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)
  4. customdried on a lyophilizer

출처 및 근거

ORD 기록
ord-e7599568f39540dbbb5474cda2471b66
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08124610B2

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