Hydrochloric Acid → HCID 59205149, compound

HRID 2242052Notes

Reaction equation

HRID 2242052 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])[C:3]=1[S:14]([NH2:17])(=[O:16])=[O:15].[CH2:18]([N:25]([CH3:41])[C:26]1[CH:27]=[C:28]([NH:33][C:34]2[N:39]=[C:38](Cl)[CH:37]=[CH:36][N:35]=2)[CH:29]=[CH:30][C:31]=1[CH3:32])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>CC(O)C>[CH2:18]([N:25]([CH3:41])[C:26]1[CH:27]=[C:28]([NH:33][C:34]2[N:35]=[C:36]([NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][C:10]([F:11])([F:13])[F:12])[C:3]=3[S:14]([NH2:17])(=[O:16])=[O:15])[CH:37]=[CH:38][N:39]=2)[CH:29]=[CH:30][C:31]=1[CH3:32])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 59205147HCID 59205147, compoundHCID 59205152HCID 59205152, compound

Product 1

HCID 59205149HCID 59205149, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 2-amino-6-(2,2,2-trifluoro-ethoxy)-benzenesulfonamide (54 mg, 0.2 mmol) and N3-benzyl-N1-(4-chloro-pyrimidin-2-yl)-N3,4-dimethyl-benzene-1,3-diamine (according to step a), 55 mg, 0.163 mmol) in 2-propanol (6 mL) and 1M HCl (0.32 mL) is heated under reflux for 1 h. Solvents are evaporated and the residue is adjusted to pH 8 by the addition of aqueous NH3. Partition between EtOAc and water, washing with 10% brine, drying of the organic phase (Na2SO4), evaporation of solvents, and chromatography (silica gel) of the residue gives 2-{2-[3-(benzyl-methyl-amino)-4-methyl-phenylamino]-pyrimidine-4-ylamino}-6-(2,2,2-trifluoro-ethoxy)-benzenesulfonamide, eluted with EtOAc/hexanes 2:3. 1H-NMR (400 MHz, DMSO-d6): 2.20 (s, CH3C(4″)); 2.43 (s, NCH3); 3.90 (s, NCH2C6H5); 4.90 (q, J=9, OCH2CF3); 6.20 (d, J=5, H—C(5′)); 6.93 and 6.97 (2d, J=9; H—C(5), H—C(5″); 7.14-7.20, 7.20-7.34, and 7.34-7.4 (3m, NCH2C6H5, H—C(2″), H—C(6″), SO2NH2); 7.45 (t, J=8, H—C(4)); 8.05 (d, J=5, H—C(6′)); 8.12 (db, J=9, H—C(3′)); 9.12 (b, NH); 8.9-10.3 (NH).

Workup

  1. temperatureunder reflux for 1 h
  2. customSolvents are evaporated
  3. additionthe residue is adjusted to pH 8 by the addition of aqueous NH3
  4. customPartition between EtOAc and water
  5. washwashing with 10% brine
  6. dry with materialdrying of the organic phase (Na2SO4), evaporation of solvents, and chromatography (silica gel) of the residue

Sources & evidence

ORD record
ord-23f95d7cacbd42658f385773c6efe082
Source dataset
uspto-grants-2010_03
Patent number
US07671063B2

Reaction notes

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