1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86656249, compound

HRID 79073Notes

Reaction equation

HRID 79073 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[C:15]2[CH:16]=[N:17][S:18][C:14]=2[CH:13]=[CH:12][C:11]=1[C:19]([OH:21])=O.C(N(C(C)C)CC)(C)C.C1C=CC2[N:39]([OH:40])N=NC=2C=1.[CH3:41][C:42]1([CH3:50])[O:46][C@H:45]([CH2:47]NO)[CH2:44][O:43]1.CCN=C=NCCCN(C)C>CN(C=O)C.C(OCC)(=O)C>[CH3:50][C:42]1([CH3:41])[O:46][C@@H:45]([CH2:47][O:40][NH:39][C:19]([C:11]2[CH:12]=[CH:13][C:14]3[S:18][N:17]=[CH:16][C:15]=3[C:10]=2[NH:9][C:3]2[CH:4]=[CH:5][C:6]([I:8])=[CH:7][C:2]=2[F:1])=[O:21])[CH2:44][O:43]1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 23541087(S)-(+)-2,2-Dimethyl-4-hydroxyaminomethyl-1,3-dioxolaneHCID 670836404-(2-Fluoro-4-iodo-phenylamino)-benzo[d]isothiazole-5-carboxylic acid

Product 1

HCID 86656249HCID 86656249, compoundYield 43.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(2-fluoro-4-iodo-phenylamino)-benzo[d]iso-thiazole-5-carboxylic acid (250 mg, 0.604 mmol), diisopropylethylamine (0.42 mL, 2.42 mmol), HOBt (163 mg, 0.1.21 mmol) and O—(((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-hydroxylamine (178 mg, 1.21 mmol) in DMF (2 mL) was added EDCI (232 mg, 1.21 mmol). The reaction mixture was stirred for 16 hours at room temperature, diluted with ethyl acetate, and washed with water, a saturated aqueous solution of sodium hydrogen carbonate, then brine before being dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue was subjected to flash chromatography (Si—PPC, gradient 0% to 50%, EtOAc in cyclohexane) to afford the title compound as a solid (142 mg, 43%). LCMS (method B): RT=3.92 min, [M+H]+=544.

Workup

  1. washwashed with water
  2. dry with materiala saturated aqueous solution of sodium hydrogen carbonate, then brine before being dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7fcc68027f4c4030b17169ff07a82d27
Source dataset
uspto-grants-2014_09
Patent number
US08841462B2

Reaction notes

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