Methylamine → HCID 86723989, compound

HRID 1475375Notes

Reaction equation

C[O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][N:11]2[C:14](=[O:30])[CH2:15][N:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C@H:18]([CH3:29])[CH2:17]2)=[CH:7][CH:6]=1)=O.[CH3:31][NH2:32]>CO>[C:25]([O:24][C:22]([N:19]1[CH2:20][CH2:21][N:16]([CH2:15][C:14]([N:11]2[C:12]3[C:8](=[CH:7][CH:6]=[C:5]([C:3](=[O:2])[NH:32][CH3:31])[CH:13]=3)[CH2:9][CH2:10]2)=[O:30])[CH2:17][C@H:18]1[CH3:29])=[O:23])([CH3:27])([CH3:26])[CH3:28]

Participants

Conditions

Temperature: 120 °C

Procedure

1-[2-((R)-4-tert-Butoxycarbonyl-3-methyl-piperazin-1-yl)-acetyl]-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester (200 mg, 0.48 mmol) was dissolved in 2.0 M methylamine in MeOH (2.4 mL) and heated under microwave irradiation at 120° C. for 4 h. The solvent was removed in vacuo and the resulting oil was purified by column chromatography on silica gel (gradient elution, 0-100% EtOAc/petrol), to give the title compound (39 mg, 20%) as a colourless solid, 1H NMR (Me-d3-OD): 8.58 (1H, s), 7.51 (1H, d), 7.33 (1H, d), 4.39-4.28 (2H, m), 4.23 (1H, d), 3.88-3.77 (1H, m), 3.31-3.14 (3H, m), 2.92 (3H, s), 2.84 (1H, d), 2.39-2.30 (1H, m), 2.24-2.12 (1H, m), 1.48 (9H, s), 1.30 (3H, d).

Workup

customThe solvent was removed in vacuo
customthe resulting oil was purified by column chromatography on silica gel (gradient elution, 0-100% EtOAc/petrol)

Sources & evidence

ORD record: ord-a06c8cb854984062b4bc30040208c2a3
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018214B2

Reaction notes

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