Hydrochloric Acid → N-{2-[5-Chloro-2-(3-oxo-2,3,4,5-tetrahydro-1H-benzo[e][1,3]diazepin-7-ylamino)-pyrimidin-4-ylamino]-phenyl}-methanesulfonamide

HRID 1687034Notes

Reaction equation

HRID 1687034 reaction equation
[NH2:1][C:2]1[CH:13]=[CH:12][C:5]2[CH2:6][NH:7][C:8](=[O:11])[NH:9][CH2:10][C:4]=2[CH:3]=1.Cl[C:15]1[N:20]=[C:19]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[C:18]([Cl:33])=[CH:17][N:16]=1.Cl.O1CCOCC1.Cl>C(O)(C)C>[Cl:33][C:18]1[C:19]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[NH:28][S:29]([CH3:32])(=[O:31])=[O:30])=[N:20][C:15]([NH:1][C:2]2[CH:13]=[CH:12][C:5]3[CH2:6][NH:7][C:8](=[O:11])[NH:9][CH2:10][C:4]=3[CH:3]=2)=[N:16][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 204431481,4-Dioxane hydrochlorideHCID 578538687-Amino-1,2,4,5-tetrahydro-(2,4)-benzodiazepin-3-oneHCID 58236399HCID 58236399, compound

Product 1

HCID 66830023N-{2-[5-Chloro-2-(3-oxo-2,3,4,5-tetrahydro-1H-benzo[e][1,3]diazepin-7-ylamino)-pyrimidin-4-ylamino]-phenyl}-methanesulfonamideYield 1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 7-amino-1,2,4,5-tetrahydro-(2,4)-benzodiazepin-3-one (75.0 mg, 0.42 mmol) in isopropanol (3 mL) was treated with N-[2-(2,5-Dichloro-pyrimidin-4-ylamino)-phenyl]-methanesulfonamide (140.2 mg, 0.42 mmol) and 4N HCl/Dioxane (0.106 mL, 0.50 mmol). The reaction mixture was irradiated at 130° C. for a total of 60 minutes. The reaction mixture was then reduced en vacuo and the product was purified and isolated flash column chromatography (0% MeOH/DCM-15% MeOH/DCM) to afford 1.98 mg of N-{2-[5-Chloro-2-(3-oxo-2,3,4,5-tetrahydro-1H-benzo[e][1,3]diazepin-7-ylamino)-pyrimidin-4-ylamino]-phenyl}-methanesulfonamide as the HCl salt. The compound was isolated as a foam, LC/MS (ESI)=480.35 (M+H). 1H NMR (400 MHz, MeOD, d4) δ 7.68 (m, 2H), 7.46 (m, 1H), 7.29 (m, 2H), 7.06 (m, 4H), 6.62 (m, 1H), 4.31 (m, 2H), 4.19 (m, 2H), 3.47 (s, 1H), 3.12 (s, 1H), 2.92 (s, 3H).

Workup

  1. customThe reaction mixture was irradiated at 130° C. for a total of 60 minutes
  2. customthe product was purified
  3. customisolated flash column chromatography (0% MeOH/DCM-15% MeOH/DCM)

Sources & evidence

ORD record
ord-cbb6f0c888804d599d289f72cb771e68
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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