HCID 86689955, compound → HCID 86689956, compound

HRID 716849Notes

Reaction equation

HRID 716849 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]([CH2:24][CH2:25][Cl:26])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-])=O)[CH:16]=2)=[O:13])=[CH:7][CH:6]=1>C(OCC)(=O)C.[Pd]>[NH2:21][C:17]1[CH:16]=[C:15]([NH:14][C:12]([NH:11][C:8]2[CH:9]=[CH:10][C:5]([N:4]([CH2:3][CH2:2][Cl:1])[CH2:24][CH2:25][Cl:26])=[CH:6][CH:7]=2)=[O:13])[CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 1

HCID 86689955HCID 86689955, compound

Product 1

HCID 86689956HCID 86689956, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The solution of compound 45a (3.5 g, 8.8 mmol) in ethyl acetate (100 mL) was hydrogenated with H2 gas in Parr hydrogenator using 10% Pd—C (0.8 g) as a catalyst at 30-35 psi for 6-7 hours. After completion of the reaction, the mixture was filtered through celite pad and filtrate was evaporated to dryness under reduced pressure to afford 1-(3-aminophenyl)-3-(4-(bis(2-chloroethyl)amino)phenyl)urea (46a), 3.0 g (93%); mp 182-183° C. 1H NMR (DMSO-d6) δ: 3.66-3.72 (8H, m, CH2), 5.22 (2H, brs, NH2), 6.17-6.19 (1H, d, J=8.0 Hz, Ar—H), 6.54-6.56 (1H, d, J=7.9 Hz, Ar—H), 6.69-6.71 (2H, d, J=9.0 Hz, Ar—H), 6.86 (1H, s, Ar—H), 6.88-6.90 (1H, t, J=8.0 Hz, Ar—H), 7.25-7.28 (2H, d, J=8.9 Hz, Ar—H), 8.27 (2H, br s, NH).

Workup

  1. customfor 6-7 hours
  2. customAfter completion of the reaction
  3. filtrationthe mixture was filtered through celite pad and filtrate
  4. customwas evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-6f4989475a7d419c8a5a7cf8a830c1c0
Source dataset
uspto-grants-2015_11
Patent number
US09193687B2

Reaction notes

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