Triethylamine → 2-Chloromethyl-N-[4-(2-furyl)-5-morpholinothiazol-2-yl]pyridine-5-carboxamide

HRID 337408노트

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HRID 337408 반응식
[Cl:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][N:4]=1.[NH2:12][C:13]1[S:14][C:15]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[C:16]([C:18]2[O:19][CH:20]=[CH:21][CH:22]=2)[N:17]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.O>[Cl:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH:12][C:13]2[S:14][C:15]([N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)=[C:16]([C:18]3[O:19][CH:20]=[CH:21][CH:22]=3)[N:17]=2)=[O:9])=[CH:5][N:4]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 2724699PyBOPHCID 149805376-(Chloromethyl)nicotinic acidHCID 231441582-Amino-4-(2-furyl)-5-morpholinothiazole

생성물 1

HCID 231442482-Chloromethyl-N-[4-(2-furyl)-5-morpholinothiazol-2-yl]pyridine-5-carboxamide수율 48%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

6-(Chloromethyl)nicotinic acid (172 mg, 1.00 mmol) obtained in Step 1, 2-amino-4-(2-furyl)-5-morpholinothiazole (251 mg, 1.00 mmol) obtained in Step 1 of Example 29 and PyBOP (572 mg, 1.10 mmol) were dissolved in DMF (4 mL), and triethylamine (0.307 mL, 2.20 mmol) was added thereto, followed by stirring at room temperature for 2 hours. The reaction mixture was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under the reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=2:1 to 1:3) to afford the entitled Compound 36 (194 mg, 48%).

후처리

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away under the reduced pressure
  5. customThe resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=2:1 to 1:3)

출처 및 근거

ORD 기록
ord-c6dd12a907d64146a3a7ef058ccba58e
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889718B2

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