1-(2-Chloroacetyl)indoline → N-({4-[2-(2,3-Dihydro-1H-indol-1-yl)-2-oxoethyl]morpholin-2-yl}methyl)-N'-phenylurea

HRID 1371410Notes

Reaction equation

HRID 1371410 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH:3]([CH2:7][NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:10])[CH2:2]1.Cl[CH2:19][C:20]([N:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24][CH2:23]1)=[O:21]>CN(C)C=O>[N:22]1([C:20](=[O:21])[CH2:19][N:1]2[CH2:6][CH2:5][O:4][CH:3]([CH2:7][NH:8][C:9]([NH:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:10])[CH2:2]2)[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 1768971-(2-Chloroacetyl)indolineHCID 23089251N-(Morpholin-2-ylmethyl)-N'-phenylurea

Product 1

HCID 10222246N-({4-[2-(2,3-Dihydro-1H-indol-1-yl)-2-oxoethyl]morpholin-2-yl}methyl)-N'-phenylureaYield 71.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of Intermediate 7 (0.01 g) in N,N-dimethylformamide (0.5 ml) was added 1-(2-chloroacetyl)indoline (0.0092 g). The mixture was stirred at 22° C. for 17 h before tris-(2-aminoethyl)amine polystyrene (Argonaut Technologies, 0.01 g @ 4.46 mmol/g) and polystyrene methyl isocyanate (Argonaut Technologies, 0.033 g @ 1.39 mmol/g) was added. Stirring was continued for a further 30 min before the mixture was purified by solid phase extraction (1 g Isolute SCX sulphonic acid column), eluting with methanol followed by 10% 0.880 ammonia solution in methanol. The basic fraction was evaporated in vacuo to give the title compound as a white solid (0.012 g). LC/MS (System A) Rt 2.69 min, Mass Spectrum m/z 394 [MH+].

Workup

  1. additionwas added
  2. customwas purified by solid phase extraction (1 g Isolute SCX sulphonic acid column)
  3. washeluting with methanol
  4. customThe basic fraction was evaporated in vacuo

Sources & evidence

ORD record
ord-f3d8f72474984646bf3d3bac1359ef4a
Source dataset
uspto-grants-2007_01
Patent number
US07157457B2

Reaction notes

Loading…