Methanol → HCID 67256219, compound

HRID 511524Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH:13]2[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]2)=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH3:12])[CH2:7]2.[C:20](=[O:23])([O-])[O-].[NH4+:24].[NH4+:25].[CH3:26][OH:27].[C-]#N.[K+]>O>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH:13]2[CH2:18][CH2:17][C:16]3([NH:25][C:26](=[O:27])[NH:24][C:20]3=[O:23])[CH2:15][CH2:14]2)=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH3:12])[CH2:7]2

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 7-amino-2-methyl-4-(4-oxocyclohexyl)-2,3-dihydro-1H-isoindol-1-one (1000.0 mg, 3.8712 mmol) and ammonium carbonate (818 mg, 8.52 mmol) in MeOH (15 mL, 370 mmol) was treated with a solution of Potassium cyanide (529 mg, 8.13 mmol) in H2O (10 mL). This mixture, which began turning white, was heated to 80° C. for 16 hours. In the morning the reaction mixture was a thick white slurry. This was transferred to a round bottom flask and concentrated to a solid which was suspended in water and collected via filtration. The filter cake washed with water two more times and once with acetone. The solid was dried under vacuum for several hours to afford the title product as 1.059 g of a pale beige solid. 1HNMR (400 MHz, DMSO-d6) δ 10.57 (br. s., 1H), 8.65 (s, 1H), 7.23 (d, J=8.34 Hz, 1H), 6.54 (d, J=8.34 Hz, 1H), 5.85 (s, 2H), 4.36 (s, 2H), 2.99 (s, 3H), 2.40-2.48 (m, 1H), 1.54-1.86 (m, 8H). MS (ES+): m/z=329.1119 [MH+]. HPLC: tR=0.96 min (UPLC TOF, polar—3 min).

Workup

customThis was transferred to a round bottom flask
concentrationconcentrated to a solid which
filtrationcollected via filtration
washThe filter cake washed with water two more times and once with acetone
customThe solid was dried under vacuum for several hours

Sources & evidence

ORD record: ord-e662e346f46641d0821356e4eefa4dcb
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096624B2

Reaction notes

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