Potassium Hydroxide → HCID 178509159, compound

HRID 2095171Notes

Reaction equation

C[O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH2:7][N:6]1[CH2:10][C:11](=[O:29])[NH:12][CH2:13][C:14]1[C:18](=[N:19][NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)[C:17]([NH2:28])=[N:16][N:15]=1)=[O:4].[OH-].[K+]>C(O)C>[NH2:28][C:17]1[C:18](=[N:19][NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)[C:14]([CH2:13][NH:12][C:11]([CH2:10][N:6]2[CH2:7][CH2:8][CH2:9][CH:5]2[C:3]([OH:4])=[O:2])=[O:29])=[N:15][N:16]=1

Participants

Conditions

Temperature: 76 °C

Procedure

1-[({5-Amino-4-[(3-fluorophenyl)hydrazono]-4H-pyrazol-3-ylmethyl}carbamoyl)-methyl]pyrrolidine-2-carboxylic acid methyl ester (80 mg, 0.20 mmole) was dissolved in 1.5 mL of 95% ethanol with KOH (19.7 mg (85%), 0.29 mmole). The solution was heated at 76° C. for 1 hour. The reaction was quenched by the addition of 1 mL of water and then acidified to pH 3 with 1.5 M HCl. The solution was evaporated to dryness together with 2-PrOH and silica gel. The resulting powder was then placed onto a silica gel column. The crude material was purified by column chromatography (CH2Cl2:MeOH:H2O:HOAc=240:60:4.7:2.2) to yield 70 mg of the title compound as a yellow powder. MS (m/z, ES−): 388 (M−1, 100%); 1H NMR (ppm, 300 MHz, DMSO-d6) δ 8.77 (br s, 1H), 7.35-7.60 (m, 3H), 7.09 (m, 1H), 6.99 (br s, 2H), 4.50 (m, 2H), 3.31 (m, 1H), 3.01 (m, 2H), 2.29 (m, 1H), 2.05 (m, 1H), 1.93 (m, 1H), 1.72 (m, 1H), 1.50-1.61 (m, 2H).

Workup

customThe reaction was quenched by the addition of 1 mL of water
customThe solution was evaporated to dryness together with 2-PrOH and silica gel
customThe crude material was purified by column chromatography (CH2Cl2:MeOH:H2O:HOAc=240:60:4.7:2.2)

Sources & evidence

ORD record: ord-923eab9d2a6f42b8ba3ee3d354e06bbd
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445694B2

Reaction notes

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