Triethylamine → HCID 59026785, compound

HRID 658389Notes

Reaction equation

HRID 658389 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:22]=[N:21][CH:20]=[CH:19][C:11]=1[C:12]([NH:14][NH:15][C:16](=[S:18])[NH2:17])=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.BrC(Br)(Br)Br.C(Br)(Br)(Br)Br.C(N(CC)CC)C>CN(C=O)C>[NH2:17][C:16]1[S:18][C:12]([C:11]2[CH:19]=[CH:20][N:21]=[CH:22][C:10]=2[NH:9][C:3]2[CH:4]=[CH:5][C:6]([I:8])=[CH:7][C:2]=2[F:1])=[N:14][N:15]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 59026765HCID 59026765, compoundHCID 86616905HCID 86616905, compound

Product 1

HCID 59026785HCID 59026785, compoundYield 4.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-{3-[(2-fluoro-4-iodophenyl)amino]isonicotinoyl}hydrazine carbothioamide (220 mg; 0.51 mmol) in DMF (5.00 mL) were added resin bound triphenylphosphine (401 mg; 1.53 mmol), carbon tetrabromide tetrabromomethane (508 mg; 1.53 mmol), and triethyl amine (180 mg; 1.53 mmol). The mixture was heated at 50° C. for 5 h. Filtered and purified on Agilent Prep. HPLC system to get 10 mg of [4-(5-Amino-[1,3,4]thiadiazol-2-yl)-pyridin-3-yl]-(2-fluoro-4-iodo-phenyl)-amine. MS m/z: 414 M+1

Workup

  1. filtrationFiltered
  2. custompurified on Agilent Prep

Sources & evidence

ORD record
ord-c8ea7fc42c4941f880ae27b8105a5f7a
Source dataset
uspto-grants-2011_12
Patent number
US08076486B2

Reaction notes

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