Dimethylamine → HCID 59026817, compound

HRID 658386Notes

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:11]=[N:12][CH:13]=[CH:14][C:15]=1[C:16]1[O:20][C:19]([NH:21][CH2:22][C:23](O)=[O:24])=[N:18][N:17]=1.[CH3:26][N:27](C=O)[CH3:28].C1N=CN(C(N2C=NC=C2)=O)C=1.CNC>>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][C:15]=1[C:16]1[O:20][C:19]([NH:21][CH2:22][C:23]([N:27]([CH3:28])[CH3:26])=[O:24])=[N:18][N:17]=1

Participants

Reactant 3

HCID 674Dimethylamine

HCID 59026822HCID 59026822, compound

HCID 86616904HCID 86616904, compound

Product 1

HCID 59026817HCID 59026817, compoundYield 45.4%

Procedure

To a solution of {5-[3-(2-Fluoro-4-iodo-phenylamino)-pyridin-4-yl]-[1,3,4]oxadiazol-2-ylamino}-acetic acid (75 mg, 0.16 mmol, 1 eq) in DMF CDI (35 mg, 0.21 mmol, 1.3 eq) was added. The reaction mixture was stirred at RT under argon for 3 hrs. Then diisopropanlethylamine (352 mg, 0.41 mmol, 2.5 eq), and dimethylamine hydrichloride (40 mg, 0.41 mmol, 2.5 eq) was added and the mixture was stirred for another 2 hrs. It was then directly purified by reverse phase preparative HPLC to give the desired product (35 mg). LC/MS (Method A) [4.87 min; 483 (M+1)]

Workup

stirringthe mixture was stirred for another 2 hrs
customIt was then directly purified by reverse phase preparative HPLC

Sources & evidence

ORD record: ord-5b0732bb515b494cb97a40c998b8ba12
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076486B2

Reaction notes

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