Chlorosulfonic acid → 4-[({6-[Cyclohexyl(cyclopropylmethyl)amino]pyrimidin-4-yl}carbonyl)amino]-3-methylbenzenesulfonyl chloride

HRID 1746658Notes

Reaction equation

HRID 1746658 reaction equation
[CH:1]1([N:7]([CH2:24][CH:25]2[CH2:27][CH2:26]2)[C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[CH3:23])=[O:15])[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:28][S:29](O)(=[O:31])=[O:30]>C(Cl)Cl>[CH:1]1([N:7]([CH2:24][CH:25]2[CH2:27][CH2:26]2)[C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([S:29]([Cl:28])(=[O:31])=[O:30])=[CH:19][C:18]=3[CH3:23])=[O:15])[CH:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acid2×HCID 594470896-[cyclohexyl(cyclopropylmethyl)amino]-N-(2-methylphenyl)pyrimidine-4-carboxamide2×

Product 1

HCID 594468814-[({6-[Cyclohexyl(cyclopropylmethyl)amino]pyrimidin-4-yl}carbonyl)amino]-3-methylbenzenesulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A cooled (−78° C.) solution of 6-[cyclohexyl(cyclopropylmethyl)amino]-N-(2-methylphenyl)pyrimidine-4-carboxamide (Intermediate 19; 2.70 g; 7.41 mmol) in DCM (27 ml) was treated dropwise with a solution of chlorosulfonic acid (2.48 ml; 37.0 mmol) in DCM (2 mL). The reaction mixture was allowed to warm to RT, then it was stirred at RT for 16 hours. The solution was cooled again (−78° C.) and treated with a second aliquot of chlorosulfonic acid (0.99 ml; 14.8 mmol) and the reaction mixture was stirred at RT for 4 h. The mixture was cooled to 5° C. and a mixture of ice/water was carefully added. The resulting precipitate was filtered and dried under vacuum to give the title compound.

Workup

  1. temperatureThe solution was cooled again (−78° C.)
  2. stirringthe reaction mixture was stirred at RT for 4 h
  3. temperatureThe mixture was cooled to 5° C.
  4. additionwas carefully added
  5. filtrationThe resulting precipitate was filtered
  6. customdried under vacuum

Sources & evidence

ORD record
ord-0f314cdb72c64f3f871b5b352bffd65f
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Reaction notes

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