Hydrochloric Acid → HCID 57636036, compound

HRID 216098Notes

Reaction equation

HRID 216098 reaction equation
N[C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]([O:14][CH3:15])[N:11]=[C:10]([NH:16][CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[ClH:27].N([O-])=O.[Na+].[S:32](=[O:34])=[O:33]>CN(C)C=O.O.C(O)(=O)C.[Cu](Cl)Cl>[CH3:15][O:14][C:12]1[N:13]=[C:8]([C:4]2[CH:3]=[C:2]([S:32]([Cl:27])(=[O:34])=[O:33])[CH:7]=[CH:6][CH:5]=2)[CH:9]=[C:10]([NH:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[N:11]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 11537596HCID 11537596, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 57636036HCID 57636036, compound

Reagents, catalysts & solvents 4

HCID 24014Cupric ChlorideCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

[6-(3-Amino-phenyl)-2-methoxy-pyrimidin-4-yl]-[2-(4-methoxy-phenyl)-ethyl]amine [1.46 g, Example 2] in dimethylformamide (4 mL) is added to concentrated hydrochloric acid and crushed ice (8 mL), The mixture is cooled to 0° C., treated with dropwise sodium nitrite (0.32 g) in water (3 mL). After stirring at 0° C. for 15 minutes this mixture is treated with a solution of copper chloride (0.36 g) in a saturated solution of sulfur dioxide in acetic acid (15 mL) previously cooled to 0° C. The reaction mixture is allowed to reach room temperature over 30 minutes and poured into water. The resulting precipitate is filtered and air dried affording 3-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzenesulfonylchloride [0.4 g, Intermediate (10)]. 1H NMR [(CD3)2SO]: δ 8 (1H, s); 7.7-7.8 (1H, m); 7.5 (1H, m); 7.2 (1H, s); 7.1 (2H, d, J=7.0); 6.8 (2H, d, J=7.0); 6.6 (1H, s); 4 (3H, s); 3.85 (3H, s); 3.7-3.8 (2H, m); 2.8 (2H, t).

Workup

  1. temperaturepreviously cooled to 0° C
  2. waitto reach room temperature over 30 minutes
  3. filtrationThe resulting precipitate is filtered
  4. customair dried

Sources & evidence

ORD record
ord-f51df306c7c64bdebe202f756404a8ae
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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