2,3-Diaminopyridine → HCID 59243189, compound

HRID 1644624Notes

Reaction equation

HRID 1644624 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([NH:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13](O)=O)(=[O:8])=[O:7].[NH2:19][C:20]1[C:25]([NH2:26])=[CH:24][CH:23]=[CH:22][N:21]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[NH:26]1[C:25]2[C:20](=[N:21][CH:22]=[CH:23][CH:24]=2)[N:19]=[C:13]1[C:12]1[CH:11]=[C:10]([NH:9][S:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)(=[O:8])=[O:7])[CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 99562,3-DiaminopyridineHCID 8000883-[(2-Thienylsulfonyl)amino]benzoic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 59243189HCID 59243189, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(thiophene-2-sulfonamido)benzoic acid (242b) was reacted with 2,3-diaminopyridine, HBTU and TEA in DMF followed by microwave as described previously for example 235. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.74 (s, 1H), 8.45 (d, 1H, J=4.6 Hz), 8.20 (d, 1H, J=7.3 Hz), 8.11 (m, 1H), 7.92 (m, 2H), 7.61 (dd, 1H, J=1.4, 3.7 Hz), 7.52 (t, 2H, J=8.0 Hz), 7.40 (dd, 1H, J=5.0, 7.8 Hz), 7.33 (dd, 1H, J=1.3, 8.0 Hz), 7.12 (dd, 1H, J=3.8, 5.0 Hz); Calc'd for C16H12N4O2S2; (M+H)=357; found 357.

Sources & evidence

ORD record
ord-5b9bab8019c74547a31fef1b847a5e1c
Source dataset
uspto-grants-2012_02
Patent number
US08124617B2

Reaction notes

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