Dimethylamine → HCID 86689958, compound

HRID 716851Notes

Reaction equation

HRID 716851 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]([CH2:26][CH2:27][Cl:28])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:25])[NH:13][C:14]2[CH:15]=[C:16]([NH:20][C:21](=[O:24])[CH2:22]Cl)[CH:17]=[CH:18][CH:19]=2)=[CH:7][CH:6]=1.[CH3:29][NH:30][CH3:31]>C1COCC1>[Cl:28][CH2:27][CH2:26][N:4]([CH2:3][CH2:2][Cl:1])[C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12](=[O:25])[NH:13][C:14]2[CH:15]=[C:16]([NH:20][C:21](=[O:24])[CH2:22][N:30]([CH3:31])[CH3:29])[CH:17]=[CH:18][CH:19]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 86689957HCID 86689957, compound

Product 1

HCID 86689958HCID 86689958, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of N-(3-(3-(4-(bis(2-chloroethyl)amino)phenyl)ureido)phenyl)-2-chloroacetamide (0.88 g, 2 mmol) in THF (50 mL) was added dropwise dimethylamine (2M solution in THF) (2 mL, 4.0 mmol). The reaction mixture was heated at 50-60° C. for overnight. After cooling the mixture, the solvent was removed by evaporation under reduced pressure. The residue obtained was triturated with saturated aqueous solution of NaHCO3. The solid product was collected by filtration, washed successively with water and hexane, and dried to yield N-(3-(3-(4-(bis(2-chloroethyl)amino)phenyl)ureido)phenyl)-2-(dimethyl-amino)acetamide (BO-2189), 0.56 g (62%), mp 62-64° C. The product was dissolved in ethanol and excess of HCl in ethylacetate was added. The solution was evaporated in vacuo to dryness and the residue was co-evaporated several times with EtOH to dryness to form BO-2189 hydrochloride. 1H NMR (DMSO-d6) δ: 2.88 (6H, s, CH3), 3.68-3.71 (8H, m, CH2), 4.13 (2H, s, CH2), 6.71-6.73 (2H, d, J=8.8 Hz, Ar—H), 7.16-7.30 (5H, m, Ar—H), 7.78 (1H, s, Ar—H), 8.95 (1H, brs, NH), 9.24 (1H, brs, NH), 9.99 (1H, brs, NH). 13C NMR (CDCl3, 125 MHz) δ: 41.09, 43.25, 52.73, 57.88, 108.84, 112.56, 113.17, 113.55, 120.03, 129.04, 138.31, 140.73, 152.86, 162.91. HRMS [ES+]: calcd for C21H27Cl2N5O2, 452.3774 [M+H]+. found 452.1620. HPLC 97.3%.

Workup

  1. temperatureAfter cooling the mixture
  2. customthe solvent was removed by evaporation under reduced pressure
  3. customThe residue obtained
  4. customwas triturated with saturated aqueous solution of NaHCO3
  5. filtrationThe solid product was collected by filtration
  6. washwashed successively with water and hexane
  7. customdried

Sources & evidence

ORD record
ord-c9d57efc79024191a641552b7ccebf0b
Source dataset
uspto-grants-2015_11
Patent number
US09193687B2

Reaction notes

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