Hydrochloric Acid → HCID 69179467, compound
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]Participants
5
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
- temperatureto cool
- filtrationthe resulting precipitate was collected by filtration
- washwas washed with ethyl acetate
- customThe crude solid was purified by chromatography
- washeluting with DCM/methanolic ammonia/(100:0)
- temperatureincreasing in polarity to (97:3)
- customThe product was recrystallized from methanol
Sources & evidence
- ORD record
- ord-a8b1071404cb491880e3613f7649aba1
- Source dataset
- uspto-grants-2005_06
- Patent number
- US06908920B2
Reaction notes
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