Hydrochloric Acid → HCID 23630234, compound

HRID 409673Notes

Reaction equation

HRID 409673 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]3[N:26]=[CH:25][N:24]=[C:23]([N:27]([CH3:44])[C:28]([NH:30][CH:31]4[C:36]([Cl:38])(C)[C:35]([O:39][CH3:40])=[CH:34][C:33]([O:41][CH3:42])=[C:32]4[Cl:43])=[O:29])[CH:22]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.Cl>[Pd].CO>[Cl:38][C:36]1[C:35]([O:39][CH3:40])=[CH:34][C:33]([O:41][CH3:42])=[C:32]([Cl:43])[C:31]=1[NH:30][C:28](=[O:29])[N:27]([CH3:44])[C:23]1[CH:22]=[C:21]([NH:20][C:17]2[CH:18]=[CH:19][C:14]([N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[CH:15][CH:16]=2)[N:26]=[CH:25][N:24]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69180028HCID 69180028, compound

Product 1

HCID 23630234HCID 23630234, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 1-{6-[4-(4-benzyl-piperazin-1-yl)-phenylamino]-pyrimidin-4-yl}-3-(2,6-dichloro-3,5-dimethoxy-6-methyl-phenyl)-1-methyl-urea (100 mg, 0.161 mmol) (Example 13), palladium on carbon (30 mg), MeOH (6 mL), and HCl (37%, 16 μL) is stirred for 5 days at RT, under a hydrogen atmosphere. The reaction mixture is filtered and concentrated. Purification of the residue by silica gel column chromatography (DCM/2N NH3 in MeOH, 95:5) affords the title compound as a beige solid: ESI-MS: 532.0/534.0 [MH]+; tR=3.39 min. (purity: 100%, system 1).

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationconcentrated
  3. customPurification of the residue by silica gel column chromatography (DCM/2N NH3 in MeOH, 95:5)

Sources & evidence

ORD record
ord-29d93923060a40de9b04937963ffdb6d
Source dataset
uspto-grants-2014_06
Patent number
US08759517B2

Reaction notes

Loading…