1,1'-Carbonyldiimidazole → HCID 66633710, compound

HRID 337187Notes

Reaction equation

HRID 337187 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:18]=[N:17][CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:31][CH:32]1[CH2:37][CH2:36][CH2:35][CH:34]([OH:38])[CH:33]1[OH:39]>CS(C)=O>[OH:39][CH:33]1[CH:34]([OH:38])[CH2:35][CH2:36][CH2:37][CH:32]1[NH:31][C:12](=[O:14])[C:11]1[CH:15]=[CH:16][N:17]=[CH:18][C:10]=1[NH:9][C:3]1[CH:4]=[CH:5][C:6]([I:8])=[CH:7][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 355714HCID 355714, compoundHCID 590267913-((2-Fluoro-4-iodophenyl)amino)isonicotinic acid

Product 1

HCID 66633710HCID 66633710, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3-(2-Fluoro-4-iodo-phenylamino)-isonicotinic acid (300 mg, 0.84 mmol.) and 1,1′-carbonylbis(1H-imidazole) (177 mg, 1.1 mmol) were suspended in DMSO (4 ml). The mixture was allowed to stir overnight (12 hr) at room temperature. 3-aminocyclohexane-1,2-diol (racemic 27/28) (110 mg, 0.84 mmol) was then added. The mixture was stirred for another 12 h at room temperature. The mixture was separated by preparative HPLC to afford two products, racemic amide (3) and racemic esters (4). LC/MS [Method A: rt: 6.01 min; m/z: 472 (M+1)]. Chiral HPLC [7.10 min, 13.12 min].

Workup

  1. stirringThe mixture was stirred for another 12 h at room temperature
  2. customThe mixture was separated by preparative HPLC

Sources & evidence

ORD record
ord-bee2e7b0c54b4624852b9b63aaa37e5a
Source dataset
uspto-grants-2014_11
Patent number
US08889719B2

Reaction notes

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