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

HRID 11139Notes

Reaction equation

HRID 11139 reaction equation
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

Participants

4

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-449db22805af466fa07da83d9037e83d
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

Loading…