O-Phenylenediamine → HCID 66831845, compound

HRID 570962Notes

Reaction equation

HRID 570962 reaction equation
[CH3:1][O:2][CH2:3][N:4]1[C:9](=[O:10])[N:8]2[CH:11]=[N:12][C:13]([C:14]([OH:16])=O)=[C:7]2[N:6]=[N:5]1.CN(C(O[N:25]1N=[N:32][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1(N)C=CC=CC=1N>CN(C=O)C>[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[NH:32][C:14]([C:13]1[N:12]=[CH:11][N:8]2[C:9](=[O:10])[N:4]([CH2:3][O:2][CH3:1])[N:5]=[N:6][C:7]=12)=[O:16]

Participants

5

Reactant 3

HCID 7243O-PhenylenediamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66831716HCID 66831716, compound

Product 1

HCID 66831845HCID 66831845, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 3-(methoxymethyl)-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic acid (512 mg; 2.28 mmol) in DMF (50 mL) was added HBTU (908 mg; 2.40 mmol). The solution was stirred for 20 minutes, then added dropwise over 20 minutes to a solution of phenylenediamine (370 mg; 6.84 mmol) in DMF (50 mL). The reaction mixture was stirred for 24 hours, then poured onto ice (1 kg), and allowed to stand until the ice had melted. The resulting orange solid was filtered, and purified by column chromatography (DCM:MeOH 98:2) to give N-(2-aminophenyl)-3-(methoxymethyl)-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide as an orange solid. (474 mg; 70%). δH (DMSO d6): 9.76 (1H, s), 8.99 (1H, s), 7.43 (1H, dd, J=7.9, 1.0), 6.99 (1H, td, J=7.6, 1.5), 6.84 (1H, dd, J=8.0, 1.3), 6.67 (1H, dd, J=7.6, 1.3), 5.64 (2H, s), 4.91 (2H, s), 3.44 (3H, s).

Workup

  1. stirringThe reaction mixture was stirred for 24 hours
  2. additionpoured onto ice (1 kg)
  3. filtrationThe resulting orange solid was filtered
  4. custompurified by column chromatography (DCM:MeOH 98:2)

Sources & evidence

ORD record
ord-d1ccb2fd74f6454b869da8d8b1dfe7a2
Source dataset
uspto-grants-2015_05
Patent number
US09024018B2

Reaction notes

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