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Triethylamine → Tris(1,1-dimethylethyl) 2-{2-chloro-5-fluoro-6-[(1,3-thiazol-4-ylmethyl)amino]-4-pyrimidinyl}-1,1,2-hydrazinetricarboxylate

HRID 1366672
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HRID 1366672 반응식
[S:1]1[CH:5]=[C:4]([CH2:6][NH2:7])[N:3]=[CH:2]1.[CH3:8][C:9]([O:12][C:13]([N:15]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[N:16]([C:24]1[C:29]([F:30])=[C:28](Cl)[N:27]=[C:26]([Cl:32])[N:25]=1)[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:14])([CH3:11])[CH3:10].C(N(CC)CC)C>C1COCC1.O>[CH3:11][C:9]([O:12][C:13]([N:15]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[N:16]([C:24]1[C:29]([F:30])=[C:28]([NH:7][CH2:6][C:4]2[N:3]=[CH:2][S:1][CH:5]=2)[N:27]=[C:26]([Cl:32])[N:25]=1)[C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])=[O:14])([CH3:8])[CH3:10]
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참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 150636521,3-Thiazol-4-ylmethanamineHCID 58000755Tris(1,1-dimethylethyl) 2-(2,6-dichloro-5-fluoro-4-pyrimidinyl)-1,1,2-hydrazinetricarboxylate

생성물 1

HCID 86637026Tris(1,1-dimethylethyl) 2-{2-chloro-5-fluoro-6-[(1,3-thiazol-4-ylmethyl)amino]-4-pyrimidinyl}-1,1,2-hydrazinetricarboxylate수율 68%

시약·촉매·용매 2

HCID 962
Water
용매
HCID 8028Tetrahydrofuran용매3회

실험 절차

To a suspension of (1,3-thiazol-4-ylmethyl)amine (0.1491 g, 1.308 mmol) in THF (10 mL) was added a solution of tris(1,1-dimethylethyl)2-(2,6-dichloro-5-fluoro-4-pyrimidinyl)-1,1,2-hydrazinetricarboxylate (0.649 g, 1.308 mmol) and triethylamine (0.22 mL, 1.5784 mmol) in THF (2 mL). Additional THF (3 mL) was added, and the reaction was stirred overnight. Then the reaction mixture was diluted with water, and the aqueous layer was extracted with ethyl acetate. The organics were dried (Na2SO4) and concentrated. The resulting crude material was purified by silica gel chromatography (0-100% ethyl acetate in hexanes) to produce tris(1,1-dimethylethyl)2-{2-chloro-5-fluoro-6-[(1,3-thiazol-4-ylmethyl)amino]-4-pyrimidinyl}-1,1,2-hydrazinetricarboxylate as a yellow oil (0.51 g, 68%). LCMS: (M-2Boc)=375.0.

후처리

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. dry with materialThe organics were dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe resulting crude material was purified by silica gel chromatography (0-100% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-5d8d4b4ffacf474db23e61dc851c9a93
출처 데이터셋
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07893056B2

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