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Tetrahydrofuran → Ethanesulfonic acid[2-fluoro-3-(7h-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-phenyl]-amide

HRID 1690032
Notes
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Reaction equation

HRID 1690032 reaction equation
[NH2:1][C:2]1[C:3]([F:19])=[C:4]([C:8]([C:10]2[C:18]3[CH:17]=[N:16][CH:15]=[N:14][C:13]=3[NH:12][CH:11]=2)=[O:9])[CH:5]=[CH:6][CH:7]=1.O1CCCC1.S(Cl)(Cl)(=O)=O.[CH2:30]([S:32](Cl)(=[O:34])=[O:33])[CH3:31]>N1C=CC=CC=1>[F:19][C:3]1[C:4]([C:8]([C:10]2[C:18]3[CH:17]=[N:16][CH:15]=[N:14][C:13]=3[NH:12][CH:11]=2)=[O:9])=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][S:32]([CH2:30][CH3:31])(=[O:34])=[O:33]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11667Ethanesulfonyl chlorideHCID 24648Sulfuryl chlorideHCID 57963256(3-amino-2-fluoro-phenyl)-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanone

Product 1

HCID 57963306Ethanesulfonic acid[2-fluoro-3-(7h-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-phenyl]-amide

Reagents, catalysts & solvents 1

HCID 1049
Pyridine
Solvent

Conditions

Temperature
60 °C

Procedure

The (3-amino-2-fluoro-phenyl)-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanone (39, 20.0 mg, 0.078 mmol) is further reacted, for example, by adding 0.5 mL of tetrahydrofuran, 50 μL of pyridine, and an appropriate sulfonyl chloride (e.g. ethanesulfonyl chloride 40, 0.078 mmol). The reaction vial is allowed to stir at room temperature or in an oil bath at 60° C. After 1-3 days, the solvents are removed under vacuum, the residue dissolved in 0.5 mL dimethyl sulfoxide, and the material purified by C18 reversed phase HPLC, eluting with 20-100% acetonitrile (with 0.1% trifluoroacetic acid) in water (with 0.1% trifluoroacetic acid) at a flow rate of 20 mL/min. Ethanesulfonic acid [2-fluoro-3-(7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-phenyl]-amide (P-0036) was prepared by this protocol using ethanesulfonyl chloride 40 in step 4. MS (ESI) [M+H+]+=349.1.

Workup

  1. customthe solvents are removed under vacuum
  2. dissolutionthe residue dissolved in 0.5 mL dimethyl sulfoxide
  3. customthe material purified by C18 reversed phase HPLC
  4. washeluting with 20-100% acetonitrile (with 0.1% trifluoroacetic acid) in water (with 0.1% trifluoroacetic acid) at a flow rate of 20 mL/min

Sources & evidence

ORD record
ord-4366c3d4cfb74cc085d697428b2f14db
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08153641B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes