Triethylamine → HCID 178509150, compound

HRID 2095173Notes

Reaction equation

[NH2:1][CH2:2][C:3]1[C:4](=[N:9][NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[C:5]([NH2:8])=[N:6][N:7]=1.C(N(CC)CC)C.S(O[CH2:36][CH2:37][O:38][CH2:39][CH2:40]OS(C1C=CC(C)=CC=1)(=O)=O)(C1C=CC(C)=CC=1)(=O)=O.C(OCC)(=O)C>CN(C=O)C>[F:17][C:13]1[CH:12]=[C:11]([NH:10][N:9]=[C:4]2[C:3]([CH2:2][N:1]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)=[N:7][N:6]=[C:5]2[NH2:8])[CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 87 °C

Procedure

To a mixture of 5-(aminomethyl)-4-(3-fluorophenylhydrazono)-3-amino-4H-pyrazole (60 mg, 0.25 mmole) and triethylamine (71 μL, 0.512 mmole) in 3 mL of anhydrous DMF was added solid di(2-tosyloxyethyl)ether (108 mg, 0.25 mmole). The reaction was heated at 87° C. for 5-6 hours, and was then worked up by the addition of saline and ethyl acetate. The crude material was purified by preparative TLC (CH2Cl2:CH3OH=15:1) to yield 13 mg of the title compound as a yellow powder. MS (m/z, ES+): 305 (M+1, 100%); 1H NMR (ppm, 300 MHz, DMSO-d6) δ 7.53 (m, 1H), 7.40 (m, 2H), 7.03 (m, 1H), 6.45 (br s, 2H), 3.97 (s, 2H), 3.74 (m, 4H), 2.65 (m, 4H).

Workup

customThe crude material was purified by preparative TLC (CH2Cl2:CH3OH=15:1)

Sources & evidence

ORD record: ord-ca3f482a4ed14e02918eb84907332356
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445694B2

Reaction notes

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