Hydrochloric Acid → 5-Cyano-4-morpholino-2-{4-[N-(3-isopropylaminopropyl)sulphamoyl]anilino}pyrimidine

HRID 1071935Notes

Reaction equation

HRID 1071935 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[C:5]([C:14]#[N:15])=[CH:4][N:3]=1.[CH:16]([NH:19][CH2:20][CH2:21][CH2:22][NH:23][S:24]([C:27]1[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=1)(=[O:26])=[O:25])([CH3:18])[CH3:17].Cl>CC(O)CC>[C:14]([C:5]1[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:7][C:2]([NH:31][C:30]2[CH:32]=[CH:33][C:27]([S:24](=[O:26])(=[O:25])[NH:23][CH2:22][CH2:21][CH2:20][NH:19][CH:16]([CH3:17])[CH3:18])=[CH:28][CH:29]=2)=[N:3][CH:4]=1)#[N:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 223905954-[N-(3-isopropylaminopropyl)sulphamoyl]anilineHCID 223906162-Chloro-5-cyano-4-morpholinopyrimidine

Product 1

HCID 223906115-Cyano-4-morpholino-2-{4-[N-(3-isopropylaminopropyl)sulphamoyl]anilino}pyrimidineYield 19%

Reagents, catalysts & solvents 1

HCID 6568(+-)-2-ButanolSolvent

Procedure

2-Chloro-5-cyano-4-morpholinopyrimidine (Method 55; 425 mg, 1.90 mmol), 4-[N-(3-isopropylaminopropyl)sulphamoyl]aniline (Method 1; 514 mg, 1.90 mmol) and 1M ethereal hydrogen chloride (189□l, 3.79 mmol) in 2-butanol (2 ml) was heated at 95° C. for 15 hours. The mixture was allowed to cool, silica was added and the volatiles were evaporated. The residue was purified by chromatography eluting with DCM/methanolic ammonia (100:0) increasing in polarity to (92:8) and the product was recrystallized from methanol to give the title compound (164 mg, 19%). NMR: 0.89 (d, 6H), 1.44 (m, 2H), 2.40 (t, 2H), 2.56 (m, 1H), 2.76 (t, 2H), 3.68-3.74 (m, 4H), 3.83-3.90 (m, 4H), 7.69 (d, 2H), 7.83 (d, 2), 8.49 (s, 1H), m/z: 460.

Workup

  1. temperatureto cool
  2. additionsilica was added
  3. customthe volatiles were evaporated
  4. customThe residue was purified by chromatography
  5. washeluting with DCM/methanolic ammonia (100:0)
  6. temperatureincreasing in polarity to (92:8)
  7. customthe product was recrystallized from methanol

Sources & evidence

ORD record
ord-b4499334dded451b99e4bb03d00c2ff5
Source dataset
uspto-grants-2005_06
Patent number
US06908920B2

Reaction notes

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