Chlorosuccinimide → HCID 45486688, compound

HRID 1362943Notes

Reaction equation

HRID 1362943 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[C:14]([C:26]3[N:27]([CH3:31])[N:28]=[CH:29][CH:30]=3)[CH:13]=2)=[O:10])=[CH:4][CH:3]=1.[Cl:32]N1C(=O)CCC1=O>CO>[Cl:32][C:30]1[CH:29]=[N:28][N:27]([CH3:31])[C:26]=1[C:14]1[CH:13]=[C:12]([NH:11][C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:10])[CH:17]=[CH:16][C:15]=1[O:18][CH2:19][CH2:20][N:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 45486694HCID 45486694, compound

Product 1

HCID 45486688HCID 45486688, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution 1-(4-chloro-phenyl)-3-[3-(2-methyl-2H-pyrazol-3-yl)-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-urea in cold methanol was added a solution of N-chloro succinimide (0.044 g, 0.3215 mmol) in methanol. The reaction mixture was stirred for 60 minutes. Then the methanol was evaporated and the residue was purified using silica flash chromatography with 15% methanol in DCM as eluant. The fractions containing the product were evaporated and dried in vacuo to afford 1-[3-(4-chloro-2-methyl-2H-pyrazol-3-yl)-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-3-(4-chloro-phenyl)-urea (Compound 17) (0.05 g, 38%) as an off-white solid. LCMS m/z (%)=474 (M+H 35Cl 35Cl, 100), 476 (M+H 35Cl, 37Cl, 81.7), 478 (M+H 37Cl 37Cl, 11.2). 1H NMR (400 MHz, DMSO-d6) δ: 8.83 (bs, 1H), 8.73 (bs, 1H), 7.61 (s, 1H), 7.54 (dd, J=2.65, 2.69 Hz, 1H), 7.46 (dd, J=2.06, 2.11 Hz, 2H), 7.37 (d, J=2.7 Hz, 1H), 7.31 (dd, J=2.09, 2.04 Hz, 2H), 7.16 (d, J=9.03 Hz, 1H), 4.2-4.0 (bm, 2H), 3.65 (s, 3H), 2.7-2.5 (bm, 2H), 2.4-2.3 (bm, 4H), 1.7-1.5 (bm, 4H).

Workup

  1. customThen the methanol was evaporated
  2. customthe residue was purified
  3. additionThe fractions containing the product
  4. customwere evaporated
  5. customdried in vacuo

Sources & evidence

ORD record
ord-20b040fc65574aed812c44968c637b90
Source dataset
uspto-grants-2011_02
Patent number
US07884101B2

Reaction notes

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