Triethylamine → HCID 11239055、化合物

HRID 987521ノート

反応式

HRID 987521 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([OH:23])=O)[CH:6]=[CH:7][C:8]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])=[O:11].[C:24]([O:28][C:29]([N:31]1[C:40]2[C:35](=[CH:36][CH:37]=[C:38]([CH2:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH:39]=2)[NH:34][CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:26])[CH3:25].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>O1CCCC1.CN(C)C1C=CN=CC=1>[C:24]([O:28][C:29]([N:31]1[C:40]2[C:35](=[CH:36][CH:37]=[C:38]([CH2:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH:39]=2)[N:34]([C:21](=[O:23])[CH2:20][C:5]2[CH:6]=[CH:7][C:8]([NH:9][C:10]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[CH3:19])=[O:11])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:26])[CH3:25]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 114498403-Methoxy-4-o-tolylureidophenylacetic acidHCID 11771978HCID 11771978、化合物

生成物 1

HCID 11239055HCID 11239055、化合物

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

A stirred solution of 3-methoxy-4-[3-o-tolyl-ureido]phenylacetic acid (0.282 g, prepared as described in Example 52B of International Patent Application Publication No. WO 96/22966) in anhydrous tetrahydrofuran (5 ml), under an atmosphere of argon and at 25° C., was treated with powdered molecular sieves 4 Å (0.5 g), 7-(2-ethoxycarbonyl-ethyl)-1,2,3,4-tetrahydro-quinoxaline-1-carboxylic acid tert-butyl ester (0.2 g, Reference Example 3), triethylamine (0,336 ml), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.273 g) and 4-dimethylaminopyridine (7 mg). After stirring at 25° C. for 3 hours the reaction mixture was filtered through a pad of celite and the filter pad was washed three times with ethyl acetate (10 ml). The combined filtrate and washings were washed twice with an aqueous saturated solution of ammonium chloride (20 ml), then with water (20 ml), then dried over magnesium sulphate and then evaporated under reduced pressure (2.7 kPa) at 40° C. The resulting white foamy solid (0.483 g) was subjected to flash chromatography on silica (0,040-0,063 mm) eluting with a mixture of cyclohexane and ethyl acetate (1:1, v/v) to give the title compound (0.3 g) as a white foamy solid. 1H NMR, 400 Hz, (CD3)2SO: δ1.2 (t, 3H); 1.5 (s, 9H); 2.3 (s, 3H); 2.65 (t, 2H); 2.9 (t, 2H); 3.65 (t, 2H); 3.85 (m, 7H); 4.1 (q, 2H); 6.7 (very broad s, 2H); 7.2 (m, 2H); 7.5 (very broad s, 1H); 7.65 (broad s, 1H); 7.8 (d, J=8 Hz, 1H); 8.05 (broad d, J=8 Hz, 1H); 8.5 (s, 1H); 8.6 (broad s, 1H). MS (CI, NH3): MNH4+ 648, MH+ 631.

後処理

  1. filtrationwas filtered through a pad of celite
  2. washthe filter pad was washed three times with ethyl acetate (10 ml)
  3. washThe combined filtrate and washings were washed twice with an aqueous saturated solution of ammonium chloride (20 ml)
  4. dry with materialwith water (20 ml), then dried over magnesium sulphate
  5. customevaporated under reduced pressure (2.7 kPa) at 40° C
  6. washeluting with a mixture of cyclohexane and ethyl acetate (1:1, v/v)

出典と根拠

ORDレコード
ord-d574fa5db46e4d4bbc8ee7f07ad0b650
出典データセット
uspto-grants-2003_10
特許番号
US06632814B1

反応ノート

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