Ethanol → tert-butyl N-[4-[3-(3-amino-5-methyl-4-pyridinyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

HRID 723109Notes

Reaction equation

HRID 723109 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12]([CH3:15])[C:13]=1I)(C)(C)C.[C:17]([O:21][C:22](=[O:45])[NH:23][C:24]([C:26]1[S:27][C:28]([S:43][CH3:44])=[C:29]([S:31]([C:34]2[CH:39]=[CH:38][C:37](O)=[C:36](B)[C:35]=2O)(=[O:33])=[O:32])[CH:30]=1)=[NH:25])([CH3:20])([CH3:19])[CH3:18].C(O)C.C1(C)C=CC=CC=1>C([O-])([O-])=O.[Na+].[Na+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(C)=O>[C:17]([O:21][C:22](=[O:45])[NH:23][C:24]([C:26]1[S:27][C:28]([S:43][CH3:44])=[C:29]([S:31]([C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([C:13]3[C:12]([CH3:15])=[CH:11][N:10]=[CH:9][C:8]=3[NH2:7])[CH:35]=2)(=[O:33])=[O:32])[CH:30]=1)=[NH:25])([CH3:20])([CH3:19])[CH3:18]

Participants

8

Reactant 4

HCID 702EthanolHCID 1140TolueneHCID 60026355(4-Iodo-5-methyl-pyridin-3-yl)-carbamic acid tert-butyl esterHCID 178419158HCID 178419158, compound

Product 1

HCID 145857697tert-butyl N-[4-[3-(3-amino-5-methyl-4-pyridinyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent

Procedure

(4-Iodo-5-methyl-pyridin-3-yl)-carbamic acid tert-butyl ester (106 mg, 0.32 mmol, Example 139: step b), {[4-(3-Boranyl-dihydroxy-benzenesulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (145 mg, 0.32 mmol, Example 140: step a) and Pd(PPh3)4 (74 mg, 0.06 mmol) were combined in aqueous Na2CO3 (2M, 1.2 mL), ethanol (1.2 mL) and toluene (2.4 mL) and was heated to 80° C. overnight. The reaction mixture was dissolved into EtOAc and washed with brine. The organic layers were dried MgSO4) and solvents were removed in vacuo. Purification by flash column chromatography (40% EtOAc/hexanes) afforded the title compound. ESI-MS (m/z): Calcd. for C28H34N4O6S3: 619.2 (M+1); found: 618.8.

Workup

  1. washwashed with brine
  2. customwere removed in vacuo
  3. customPurification by flash column chromatography (40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-573e10a53b8449fe945ce677151c8fed
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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