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Hydrochloric Acid → Taprizosin

HRID 1795391
Notes
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Reaction equation

HRID 1795391 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[C:5]([O:16][CH3:17])=[C:4]([O:18][CH3:19])[CH:3]=1.[C:20]([N:22]1[CH2:31][CH2:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][C:28]=2[NH:32][S:33]([CH3:36])(=[O:35])=[O:34])[CH2:23]1)#[N:21].O.Cl>CS(C)=O.C(OCC)(=O)C>[NH2:9][C:8]1[C:7]2[C:2](=[CH:3][C:4]([O:18][CH3:19])=[C:5]([O:16][CH3:17])[C:6]=2[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[N:1]=[C:20]([N:22]2[CH2:31][CH2:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][C:28]=3[NH:32][S:33]([CH3:36])(=[O:35])=[O:34])[CH2:23]2)[N:21]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 9856336N-(2-cyano-1,2,3,4-tetrahydro-5-isoquinolyl)methanesulfonamideHCID 99430356-Amino-3,4-dimethoxy-2-(2-pyridyl)benzonitrile

Product 1

HCID 6433102TaprizosinYield 74.6%

Reagents, catalysts & solvents 2

HCID 679
Dimethyl Sulfoxide
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 6-amino-3,4-dimethoxy-2-(2-pyridyl)benzonitrile (see Example 2 or 2A, 7 g, 27 mmol) and N-(2-cyano-1,2,3,4-tetrahydro-5-isoquinolyl)methanesulfonamide (see Example 3 or 3A, 9 g, 36 mmol) in DMSO (21 ml) at room temperature, was added sodium-t-pentoxide (9.5 g, 92 mmol) portionwise over 20 minutes keeping the temperature below 30° C. The resulting slurry was then stirred for 2 hours. After this time, iced water (35 ml) was added over 1 minute followed by ethyl acetate (35 ml) before reducing the pH of the biphasic mixture to 8.0 with 2M aqueous HCl (20 ml). The aqueous phase was extracted with ethyl acetate (50 ml). The combined organics were washed with saturated NaCl solution (2×30 ml), reduced in volume and stirred for 3 hours. After this time, the resulting slurry was filtered to yield 10.2 g (74%) of the title compound.

Workup

  1. customthe temperature below 30° C
  2. extractionThe aqueous phase was extracted with ethyl acetate (50 ml)
  3. washThe combined organics were washed with saturated NaCl solution (2×30 ml)
  4. stirringstirred for 3 hours
  5. filtrationAfter this time, the resulting slurry was filtered

Sources & evidence

ORD record
ord-960870f5b2404c689c0b1538900cccde
Source dataset
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07026479B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes