O-Phenylenediamine → HCID 58084304, compound

HRID 1853146Notes

Reaction equation

HRID 1853146 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([OH:11])=O)=[N:4][C:5]([Br:8])=[CH:6][N:7]=1.[C:12]1([NH2:19])[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH2:18].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[NH2:1][C:2]1[C:3]([C:9]([NH:18][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[NH2:19])=[O:11])=[N:4][C:5]([Br:8])=[CH:6][N:7]=1

Participants

7

Reactant 4

HCID 7243O-PhenylenediamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 185216003-Amino-6-bromopyrazine-2-carboxylic acid

Product 1

HCID 58084304HCID 58084304, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-amino-6-bromopyrazine-2-carboxylic acid (140 g, 0.64 mol), o-phenylenediamine (70 g, 0.65 mol) and TBTU (247 g, 0.77 mol) in DMF (1.5 L) at 0° C. was added drop wise DIPEA (166 g, 1.29 mol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into water and the resultant precipitate isolated by filtration and washed with water. The precipitate was dried at 50° C. to give the sub-title compound as a brown solid that was used in the next step without further purification product (140 g, 70% Yield). 1H NMR (400 MHz, DMSO) δ 4.95 (br s, 2H), 6.59 (m, 1H), 6.79 (d, 1H), 6.95 (m, 1H), 7.30 (d, 1H), 7.70 (bs, 2H), 8.40 (s, 1H) and 9.65 (s, 1H) ppm; MS (ES+) 307.8.

Sources & evidence

ORD record
ord-98a189cc4a8941a6b5edb8f7f6907282
Source dataset
uspto-grants-2015_02
Patent number
US08962631B2

Reaction notes

Loading…