Hydrochloric Acid → HCID 59205155, compound

HRID 2242053Notes

Reaction equation

HRID 2242053 reaction equation
[CH2:1]([N:8](C)[C:9]1[CH:10]=[C:11]([NH:16][C:17]2[N:22]=[C:21]([NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH2:31][C:32]([F:35])([F:34])[F:33])[C:25]=3[S:36]([NH2:39])(=[O:38])=[O:37])[CH:20]=[CH:19][N:18]=2)[CH:12]=[CH:13][C:14]=1[CH3:15])C1C=CC=CC=1.Cl>CCO.[OH-].[OH-].[Pd+2]>[CH3:15][C:14]1[CH:13]=[CH:12][C:11]([NH:16][C:17]2[N:22]=[C:21]([NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH2:31][C:32]([F:34])([F:35])[F:33])[C:25]=3[S:36]([NH2:39])(=[O:38])=[O:37])[CH:20]=[CH:19][N:18]=2)=[CH:10][C:9]=1[NH:8][CH3:1]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59205149HCID 59205149, compound

Product 1

HCID 59205155HCID 59205155, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A suspension of 44 mg 20% Pd(OH)2 on charcoal in EtOH (10 mL) is treated with H2 under vigorous stirring. To this 2-{2-[3-(benzyl-methyl-amino)-4-methyl-phenylamino]-pyrimidine-4-ylamino}-6-(2,2,2-trifluoro-ethoxy)-benzenesulfonamide (28 mg, 0.049 mmol) and 0.1 mL of 1 M HCl are added (final volume ca. 20 mL). After stirring for 30 min under H2 the catalyst is removed by filtration and the residue of the filtrate, neutralized with ammonia, is purified by chromatography (silica gel, CH2Cl2/CH3OH 95:5), yielding the title compound. 1H-NMR (400 MHz, DMSO-d6): 1.95 (s, CH3—C(4″)); 2.59 (d, J=5, NHCH3); 4.83 (q, J=5, NHCH3); 4.90 (q, J=9.4, OCH2CF3); 6.15 (d, J=6, H—C(5′)); 6.72(d, J=2, H—C(2″)); 6.75 (d, J=8.5, H—C(5″)); 6.9 (dd, J=8.5 and 2, H—C(6″)); 6.93 (d, J=8.5, H—C(5)); 6.8-7.5 (b, SO2NH2); 7.4 (t, J=8.5 H—C(4)); 8.03 (d, J=6, H—C(6′)); 8.23 (d, J=8.5, H—C(3)); 8.95 (s, NH); 9.0-10.1 (b, NH).

Workup

  1. additionis treated with H2 under vigorous stirring
  2. customis removed by filtration
  3. customis purified by chromatography (silica gel, CH2Cl2/CH3OH 95:5)

Sources & evidence

ORD record
ord-68743a5616e44be0abb97bd2d521b391
Source dataset
uspto-grants-2010_03
Patent number
US07671063B2

Reaction notes

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