Acetonitrile → 1-(4-Amino-quinazolin-7-ylmethyl)-4-[3-(4-bromo-furan-2-yl)-(E)-allyl]-piperazin-2-one

HRID 1432961ノート

反応式

HRID 1432961 の反応式
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][N:13]3[CH2:18][CH2:17][NH:16][CH2:15][C:14]3=[O:19])=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.C(#N)C.[Br:23][C:24]1[CH:25]=[C:26](/[CH:29]=[CH:30]/[CH:31]=O)[O:27][CH:28]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CC(O)=O.O.C(#N)C>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][N:13]3[CH2:18][CH2:17][N:16]([CH2:31]/[CH:30]=[CH:29]/[C:26]4[O:27][CH:28]=[C:24]([Br:23])[CH:25]=4)[CH2:15][C:14]3=[O:19])=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1

参加物

7

反応物 4

HCID 6342AcetonitrileHCID 5049666Sodium triacetoxyborohydrideHCID 179851741-(4-Aminoquinazoline-7-ylmethyl)piperazine-2-oneHCID 865925453-(4-Bromofuran-2-yl)prop-2-enal

生成物 1

HCID 671091711-(4-Amino-quinazolin-7-ylmethyl)-4-[3-(4-bromo-furan-2-yl)-(E)-allyl]-piperazin-2-one収率 35%

試薬・触媒・溶媒 2

HCID 176Acetic Acid触媒HCID 18373917Acetonitrile--water (1/1)溶媒

実験手順

To a solution of 1-(4-amino-quinazolin-7-ylmethyl)-piperazin-2-one (50 mg, 0.20 mmol), EXAMPLE 72.in 3 mL of acetonitrile is added 3-(4-bromo-furan-2-yl)-(E)-propenal (43 mg, 0.22 mmol), prepared as described in EXAMPLE 18, 2 drops of HOAc and sodium triacetoxyborohydride (62 mg, 0.29 mmol). The solution is stirred at room temperature for 16 hours. After this time, the solution is diluted with water/acetonitrile. The crude material is purified by RP-HPLC eluting in a gradient of 10% CH3CN/H2O (0.1% TFA) to 80% CH3CN/H2O (0.1% TFA) and the appropriate product fractions are combined and lyopholized to give the title compound (48 mg, 0.07 mmol) as a white solid. 1H NMR (DMSO-d6, 300 MHz) δ9.75 (bs, 2H), 8.85 (s, 1H), 8.60 (d, 1H), 7.95 (s, 1H), 7.69 (s, 1H), 7.62 (d, 1H), 6.80 (s, 1H), 6.65 (d, 1H), 6.19 (dt, 1H), 4.80 (s, 2H), 3.70 (m, 4H), 3.50 (m, 2H), 3.28 (m, 2H), ESI MS [M+H]+=441,443 (Br pattern).

後処理

  1. customprepared
  2. customThe crude material is purified by RP-HPLC
  3. washeluting in a gradient of 10% CH3CN/H2O (0.1% TFA) to 80% CH3CN/H2O (0.1% TFA)

出典と根拠

ORDレコード
ord-a21b1433faae4d10824e8ba203ef86a5
出典データセット
uspto-grants-2009_11
特許番号
US07612075B2

反応ノート

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