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Hydrochloric Acid → HCID 69179467, compound

HRID 1071936
Notes
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Reaction equation

HRID 1071936 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:5]([C:18]#[N:19])=[CH:4][N:3]=1.[O:20]1[CH2:24][CH2:23][CH2:22][CH:21]1[CH2:25][NH:26][S:27]([C:30]1[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=1)(=[O:29])=[O:28].Cl>CC(O)CC>[C:18]([C:5]1[C:6]([NH:8][CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[N:7][C:2]([NH:34][C:33]2[CH:32]=[CH:31][C:30]([S:27](=[O:29])(=[O:28])[NH:26][CH2:25][CH:21]3[CH2:22][CH2:23][CH2:24][O:20]3)=[CH:36][CH:35]=2)=[N:3][CH:4]=1)#[N:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 47135324-amino-N-(tetrahydrofuran-2-ylmethyl)benzenesulfonamideHCID 22390639HCID 22390639, compound

Product 1

HCID 69179467HCID 69179467, compoundYield 13.2%

Reagents, catalysts & solvents 1

HCID 6568(+-)-2-ButanolSolvent

Procedure

2Chloro-5-cyano-4-(3-morpholinopropylamino)pyrimidine (Method 66; 525 mg, 1.87 mmol), 4-[N-(tetrahydrofur-2-ylmethyl)sulphamoyl]aniline (Method 2; 430 mg, 1.68 mmol) and 1M ethereal hydrogen chloride (1.87 ml, 1.87 mmol) in 2-butanol (3 ml) was heated at 90° C. for 3 hours. The mixture was allowed to cool, the resulting precipitate was collected by filtration and was washed with ethyl acetate. The crude solid was purified by chromatography eluting with DCM/methanolic ammonia/(100:0) increasing in polarity to (97:3). The product was recrystallized from methanol to give the title compound (111 mg).

Workup

  1. temperatureto cool
  2. filtrationthe resulting precipitate was collected by filtration
  3. washwas washed with ethyl acetate
  4. customThe crude solid was purified by chromatography
  5. washeluting with DCM/methanolic ammonia/(100:0)
  6. temperatureincreasing in polarity to (97:3)
  7. customThe product was recrystallized from methanol

Sources & evidence

ORD record
ord-a8b1071404cb491880e3613f7649aba1
Source dataset
uspto-grants-2005_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06908920B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes