Triethylamine → HCID 58739064, 화합물

HRID 720279노트

반응식

HRID 720279 반응식
[O:1]=[S:2]1(=[O:21])[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[N:9]([CH3:20])[C:10](=[O:19])[C:11]([O:17][CH3:18])=[C:12]([C:14]([OH:16])=O)[N:13]=1.[F:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][NH2:28])=[CH:25][CH:24]=1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1>C(#N)C.C(OCC)(=O)C>[F:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][NH:28][C:14]([C:12]2[N:13]=[C:8]([N:3]3[CH2:4][CH2:5][CH2:6][CH2:7][S:2]3(=[O:1])=[O:21])[N:9]([CH3:20])[C:10](=[O:19])[C:11]=2[O:17][CH3:18])=[O:16])=[CH:25][CH:24]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 673264-FluorobenzylamineHCID 2724699PyBOPHCID 58739076HCID 58739076, 화합물

생성물 1

HCID 58739064HCID 58739064, 화합물수율 92.6%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 2-(1,1-dioxo-1λ6-[1,2]thiazinan-2-yl)-5-methoxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid (0.235 g, 0.74 mmol) and 4-fluorobenzylamine (0.14 g, 1.13 mmol) in acetonitrile (10 ml) was treated at 22° C. with triethylamine (0.32 ml, 2.3 mmol) followed by benzotriazole-1-yloxy-tris-pyrrolidino-phosphonium hexafluorophosphate (0.42 g, 0.81 mmol) and the resulting mixture was stirred for 3 h. The reaction mixture was then diluted with ethyl acetate, washed with saturated sodium bicarbonate, brine and dried over anhydrous magnesium sulfate. Evaporation of the solvent and chromatography of the residue on silica gel (elution toluene-ethyl acetate 1:1 to ethyl acetate) gave 0.291 g (92% yield) of the title amide as a white solid. 1HNMR 400 MHz (CDCl3) δ (ppm): 1.6–1.7 and 2.3–2.5 (4H, m, 2×CH2), 3.2 and 3.5 (2×1H, m, CH2), 3.62 (3H, s, NCH3), 3.7 and 3.95 (2×1H, m, CH2), 4.04 (3H, s, OCH3), 4.59 (2H, d, J=5.8 Hz, NCH2), 7.04 (2H, m, aromatics), 7.31 (2H, m, aromatics), 7.75 (1H, broad, NH). HRMS (FAB POS) calculated for C18H22FN4O5S [M+H+]: 425.129495. found: 425.129040.

후처리

  1. washwashed with saturated sodium bicarbonate, brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customEvaporation of the solvent and chromatography of the residue on silica gel (elution toluene-ethyl acetate 1:1 to ethyl acetate)

출처 및 근거

ORD 기록
ord-bc8c66f5aab0407c85ecf7cdd5995915
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07135467B2

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