Dimethylamine → 4-(2-Chlorophenyl)-8-[3-(dimethylamino)propoxy]-9-methoxy-1h-[1]benzofuro[3,2-e]isoindole-1,3(2h)-dione

HRID 11139ノート

反応式

HRID 11139 の反応式
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:11]([O:12][CH3:13])=[CH:10][C:9]2[C:14]3[C:15]4[C:16](=[O:36])[N:17](CCCBr)[C:18](=[O:31])[C:19]=4[C:20]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[Cl:30])=[CH:21][C:22]=3[O:23][C:8]=2[CH:7]=1.[CH3:37][NH:38][CH3:39]>O1CCCC1>[Cl:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[C:20]1[C:19]2[C:18](=[O:31])[NH:17][C:16](=[O:36])[C:15]=2[C:14]2[C:9]3[CH:10]=[C:11]([O:12][CH3:13])[C:6]([O:5][CH2:4][CH2:3][CH2:2][N:38]([CH3:39])[CH3:37])=[CH:7][C:8]=3[O:23][C:22]=2[CH:21]=1

参加物

4

反応物 2

HCID 674DimethylamineHCID 219808488-(3-Bromopropoxy)-2-(3-bromopropyl)-4-(2-chlorophenyl)-9-methoxy-1h-[1]benzofuro[3,2-e]isoindole-1,3(2h)-dione

生成物 1

HCID 219808044-(2-Chlorophenyl)-8-[3-(dimethylamino)propoxy]-9-methoxy-1h-[1]benzofuro[3,2-e]isoindole-1,3(2h)-dione収率 84%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Reaction of dibromide (331) (100 mg, 0.16 mmol) prepared as described in example 385 with aqueous dimethylamine solution (40%, 5.0 mL) according to The procedure described in example 179, except that the reaction was performed in tetrahydrofuran (50 mL) at room temperature for 30 hours, gave the crude diamine (LXXX; Ar=2-chlorophenyl, n=3, Z═N(CH3)2), which was used without further purification as a tetrahydrofuran solution. To this solution was added SN potassium hydroxide (2.5 mL), then the procedure outlined in example 328 was followed except that the HCl treatment was for 24 hours and the chromatography was performed eluting with methanol/dichloromethane/concentrated ammonia (15:85:trace). Trituration from ethyl acetate gave amine (332) (64 mg, 84%) as a yellow powder, mp 251–253° C. 1H NMR δ [(CD3)2SO] 11.37 (br s, 1H), 8.15 (s, 1H), 7.93 (s, 1H), 7.59 (m, 1H), 7.55 (s, 1H), 7.52–7.43 (m, 3H), 4.18 (t, J=6.4 Hz, 2H),3.93 (s, 3H), ˜2.5 (obscured m, 2H), 2.23 (br s, 6H), 1.96 (m, 2H). Found: C, 65.03; H, 4.79; N, 6.00. C26H23ClN2O5 requires: C, 65.21; H, 4.84; N, 5.85.

後処理

  1. customprepared
  2. customgave the crude diamine (LXXX; Ar=2-chlorophenyl, n=3, Z═N(CH3)2), which
  3. customwas used without further purification as a tetrahydrofuran solution
  4. additionTo this solution was added SN potassium hydroxide (2.5 mL)
  5. washthe chromatography was performed eluting with methanol/dichloromethane/concentrated ammonia (15:85:trace)

出典と根拠

ORDレコード
ord-449db22805af466fa07da83d9037e83d
出典データセット
uspto-grants-2006_08
特許番号
US07094798B1

反応ノート

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