Sulfamic Acid → HCID 59837602, compound

HRID 273537Notes

Reaction equation

[CH3:1][C:2]1[C:7]2[N:8]=[C:9]([NH2:12])[N:10]=[N:11][C:6]=2[CH:5]=[C:4]([C:13]2[C:14]([CH3:19])=[N:15][O:16][C:17]=2[CH3:18])[CH:3]=1.S(=O)(=O)(O)N.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30](N)=[CH:29][CH:28]=1>>[CH3:19][C:14]1[C:13]([C:4]2[CH:3]=[C:2]([CH3:1])[C:7]3[N:8]=[C:9]([NH:12][C:30]4[CH:31]=[CH:32][C:27]([O:26][CH3:25])=[CH:28][CH:29]=4)[N:10]=[N:11][C:6]=3[CH:5]=2)=[C:17]([CH3:18])[O:16][N:15]=1

Participants

Reactant 3

HCID 5987Sulfamic Acid

HCID 7732P-Anisidine

HCID 598377647-(3,5-Dimethyl-4-isoxazolyl)-5-methyl-1,2,4-benzotriazin-3-amine2×

Product 1

HCID 59837602HCID 59837602, compoundYield 32.1%

Conditions

Temperature: 180 °C

Procedure

The mixture of 5-methyl-7-(3,5-dimethylisoxazol-4-yl)benzo[e][1,2,4]triazin-3-amine (compound 7 on scheme (CXXVIII)) (107 mg, 0.42 mmol), sulfamic acid (81.4 mg, 0.84 mmol), and 4-methoxybenzenamine 8 (774 mg, 6.3 mmol) was heated at 180° C. overnight. The product was purified by chromatography (SiO2/CH2Cl2) and the title product (48.7 mg, 32%) was obtained as a yellow solid. 1H NMR (CD2Cl2): δ 2.34 (s, 3H); 2.49 (s, 3H); 2.70 (s, 3H); 3.84 (s, 3H); 6.99 (d, J=8.9 Hz, 2H); 7.57 (s, 1H); 7.83 (d, J=8.9 Hz, 2H); 8.03 (s, 1H); 8.10 (br, 1H). MS (ESI+): m/z=362.1.

Workup

customThe product was purified by chromatography (SiO2/CH2Cl2)

Sources & evidence

ORD record: ord-f230fcfb90c346b2a382b85f069bbb3c
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07456176B2

Reaction notes

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