Triethylamine → HCID 58739064、化合物

HRID 720279ノート

反応式

HRID 720279 の反応式
[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

参加物

7

反応物 4

HCID 8471TriethylamineHCID 673264-FluorobenzylamineHCID 2724699PyBOPHCID 58739076HCID 58739076、化合物

生成物 1

HCID 58739064HCID 58739064、化合物収率 92.6%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-bc8c66f5aab0407c85ecf7cdd5995915
出典データセット
uspto-grants-2006_11
特許番号
US07135467B2

反応ノート

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