2,3-Diaminopyridine → HCID 59243043, compound

HRID 1644622Notes

Reaction equation

HRID 1644622 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([N+:15]([O-])=O)[CH:14]=1)[C:9](O)=O.[NH2:22][C:23]1[C:28]([NH2:29])=[CH:27][CH:26]=[CH:25][N:24]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N1C2C=CC=NC=2N=C1.[Sn](Cl)Cl.[S:66]1[CH:70]=[CH:69][CH:68]=[C:67]1[S:71](Cl)(=[O:73])=[O:72]>C(O)C.C(O)CCC.CN(C=O)C>[F:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][O:5][C:6]1[CH:14]=[C:13]([NH:15][S:71]([C:67]2[S:66][CH:70]=[CH:69][CH:68]=2)(=[O:73])=[O:72])[CH:12]=[C:8]([C:9]2[NH:29][C:28]3[C:23]([N:22]=2)=[N:24][CH:25]=[CH:26][CH:27]=3)[CH:7]=1

Participants

10

Reactant 6

HCID 99562,3-DiaminopyridineHCID 24479Stannous ChlorideHCID 67504Imidazo(4,5-b)pyridineHCID 855182-Thiophenesulfonyl chlorideHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66775223HCID 66775223, compound

Product 1

HCID 59243043HCID 59243043, compound

Reagents, catalysts & solvents 3

HCID 2631-ButanolSolventHCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

The subsequent steps have been described previously and include formation of the amide (LC/MS calculated and found 383) from the 3-(2-fluorobenzyloxy)-5-nitrobenzoic acid and 2,3-diaminopyridine with HBTU, TEA, and DMF followed by cyclization to the imidazopyridine (LC/MS calculated and found 365) in the microwave at 180° C. in 1:1 BuOH-glacial acetic acid for 30 min. Finally, the nitro group was reduced to the amine using tin (II) chloride in refluxing ethyl alcohol (LC/MS calculated and found 335) and the resulting amine was reacted with 2-thiophene sulfonyl chloride to form the sulfonamide final product (LC/MS calculated and found 481). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.45 (m, 1H), 7.84 (m, 1H), 7.70 (m, 2H), 7.59 (m, 3H), 7.5-7.2 (m, 5H), 7.06 (m, 1H), 6.99 (m, 1H), 6.71 (m, 1H), 5.16 (s, 2H); Calc'd for C23H17FN4O3S2; m/z (M+H+)=481; found 481.

Sources & evidence

ORD record
ord-b7cc349aec5c438c8eb6a9811a5133ab
Source dataset
uspto-grants-2012_02
Patent number
US08124617B2

Reaction notes

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