Acetic Acid → HCID 58465715, compound

HRID 1842456Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([N:9]1[CH2:15][CH2:14][CH2:13][N:12]2[CH:16]=[C:17]([C:19]([O:21]CC)=O)[CH:18]=[C:11]2[CH2:10]1)=[O:8].[OH-:24].[K+].Cl.[NH2:27]O.C(O)(=O)C>CO>[OH:24][NH:27][C:19]([C:17]1[CH:18]=[C:11]2[CH2:10][N:9]([C:7]([C:3]3[N:2]([CH3:1])[CH:6]=[CH:5][CH:4]=3)=[O:8])[CH2:15][CH2:14][CH2:13][N:12]2[CH:16]=1)=[O:21]

Participants

Conditions

Temperature: 80 °C

Procedure

To a vial containing crude ethyl 2-(1-methyl-1H-pyrrole-2-carbonyl)-2,3,4,5-tetrahydro-1H-pyrrolo[1,2-a][1,4]diazepine-8-carboxylate from Step 1 above was added potassium hydroxide (0.112 g, 2 mmol), hydroxylamine hydrochloride (0.0417 g, 0.6 mmol), and methanol (2 mL). The mixture was shaken at 80° C. for 2 h then cooled to room temperature. Acetic acid (0.114 mL, 2 mmol) was added to quench the excess base. The solvent was then completely evaporated and to the residue was added DMSO (1.2 mL). After filtration, the solution was purified via Gilson prep-HPLC to give N-hydroxy-2-(1-methyl-1H-pyrrole-2-carbonyl)-2,3,4,5-tetrahydro-1H-pyrrolo[1,2-a][1,4]diazepine-8-carboxamide (0.004 g, 6.5%). LC-MS (FA): ES+303; 1H NMR (CD3CN, 400 MHz) δ6.81 (s, 1 H), 6.40 (s, 1 H), 5.95 (m, 1 H), 5.81 (m, 1 H), 5.70 (m, 1 H), 4.27 (s, 2 H), 3.83 (m, 2 H), 3.51 (m, 2 H), 3.21 (s, 3 H), 1.85 (m, 2 H).

Workup

temperaturethen cooled to room temperature
customto quench the excess base
customThe solvent was then completely evaporated and to the residue
additionwas added DMSO (1.2 mL)
filtrationAfter filtration
customthe solution was purified via Gilson prep-HPLC

Sources & evidence

ORD record: ord-e2381bd6d7834d4d8f24a139e7b06744
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946223B2

Reaction notes

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