Guanidine → HCID 22480344, compound

HRID 1349708Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17](=O)[CH3:18])[CH:15]=3)[NH:10][N:9]=2)=[CH:4][CH:3]=1.[NH2:20][C:21]([NH2:23])=[NH:22].C[O-].[Na+].F[C:28](F)(F)C(O)=O>CC#N.O.CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]4[CH:18]=[CH:28][N:20]=[C:21]([NH2:23])[N:22]=4)[CH:15]=3)[NH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A solution of 1-[3-(4-fluorophenyl)-1H-indazol-5-yl]ethan-1-one (73 mg, 0.29 mmol) in dimethoxy DMF acetal (25 mL) was heated to 90° C. overnight. The solution was then concentrated to an oil under vacuo when methanol (10 mL), guanidine (55 mg, 0.57 mmol), and NaOMe (290 μL of a 2 N solution, 0.58 mmol) was added. The reaction was then heated in a sealed tube to 120° C. overnight. The reaction was then acidified with trifluoroacetic acid then subjected to preparative HPLC (CH3CN/water 0.1% TFA) to recover the final compound (3 mg, 3% yield). 1H NMR (DMSO-d6) δ 13.5 (br s, 1H), 8.78 (s, 1H), 8.35 (d, 1H), 8.19 (d, 1H), 8.06 (dd, 2H), 7.72 (d, 1H), 7.53 (d, 1H), 7.38 (t, 2H); ES-MS (m/z) 306 [M+1]+.

Workup

additionwas added

Sources & evidence

ORD record: ord-6579af43b34648a39f7785f46252ed22
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07211594B2

Reaction notes

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