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Diisopropylethylamine → (S)-6-amino-5-iodo-N-[methyl(oxo)phenyl-lambda6-sulfanylidene]nicotinamide

HRID 391559
Notes
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Reaction equation

HRID 391559 reaction equation
[NH2:1][C:2]1[C:10]([I:11])=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.C(N(CC)C(C)C)(C)C.[CH3:21][S@:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[NH:24])=[O:23].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C.CCOC(C)=O>[NH2:1][C:2]1[C:10]([I:11])=[CH:9][C:5]([C:6]([N:24]=[S@@:22]([CH3:21])(=[O:23])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:8])=[CH:4][N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 114255416-Amino-5-iodonicotinic acidHCID 25036288(S)-(+)-S-Methyl-S-phenylsulfoximine

Product 1

HCID 86629469(S)-6-amino-5-iodo-N-[methyl(oxo)phenyl-lambda6-sulfanylidene]nicotinamideYield 71%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 6-amino-5-iodonicotinic acid (330 mg, 1.3 mmol), N,N-diisopropylethylamine (0.44 mL, 2.5 mmol), and (S)-(+)-S-methyl-S-phenylsulfoximine (291 mg, 1.9 mmol) in 7.0 mL DMF at room temperature was added BOP (608 mg, 1.4 mmol). The solution was stirred 10 minutes and then heated at 60° C. for 5 hours. The mixture was dissolved in EtOAc, washed with Na2CO3 solution, H2O, brine, dried with anhydrous Na2SO4 and rotary evaporated. The brown oil was purified by chromatography (silica gel, hexane/acetone). The product containing fractions were purified by chromatography one additional time (silica gel, EtOAc/MeOH). To give the title compound as a white foam (354 mg, 71%).

Workup

  1. washwashed with Na2CO3 solution, H2O, brine
  2. dry with materialdried with anhydrous Na2SO4 and rotary evaporated
  3. customThe brown oil was purified by chromatography (silica gel, hexane/acetone)
  4. additionThe product containing fractions
  5. customwere purified by chromatography one additional time (silica gel, EtOAc/MeOH)

Sources & evidence

ORD record
ord-6c7dee40b49b47feb358646768ca674e
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08383825B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes