Chlorosuccinimide → HCID 45486688, compound

HRID 1626169Notes

Reaction equation

HRID 1626169 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 of 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+H35Cl35Cl, 100), 476 (M+H35Cl37Cl, 81.7), 478 (M+H37Cl37Cl, 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-86ff1129fd7d4b3c9dd895d1f9fd9f34
Source dataset
uspto-grants-2014_07
Patent number
US08785441B2

Reaction notes

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