Isoamylamine → HCID 178467589, compound

HRID 2173997Notes

Reaction equation

[OH:1][CH:2]([C:14]1[C:22]([CH2:23][O:24][C:25]2C=CC=C[CH:26]=2)=[CH:21][C:20]([CH3:31])=[C:19]2[C:15]=1[CH:16]=[CH:17][N:18]2S(C1C=CC(C)=CC=1)(=O)=O)[C:3]1[NH:7][C:6]2[CH:8]=[CH:9][C:10]([C:12]#[N:13])=[CH:11][C:5]=2[N:4]=1.C(N)CC(C)C.[OH-].[K+]>CCO.C(Cl)Cl>[CH2:25]([O:24][CH2:23][C:22]1[C:14]([CH:2]([OH:1])[C:3]2[NH:7][C:6]3[CH:8]=[CH:9][C:10]([C:12]#[N:13])=[CH:11][C:5]=3[N:4]=2)=[C:15]2[C:19](=[C:20]([CH3:31])[CH:21]=1)[NH:18][CH:17]=[CH:16]2)[CH3:26]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-(hydroxy(7-methyl-5-(phenoxymethyl)-1-tosyl-1H-indol-4-yl)methyl)-1H-benzo[d]imidazole-5-carbonitrile (130 mg, 0.23 mmol) in EtOH (3 mL), isoamylamine (101 mg, 1.15 mmol), and KOH (64.8 mg, 1.15 mmol) were added and the reaction stirred at 100° C. for 1.5 h under microwave irradiation. The reaction mixture was diluted with CH2Cl2 filtered through SiO2. The SiO2 cake was washed with a mixture of CH2Cl2/MeOH (c.a. 6/1). The organic solution was concentrated and purified by RP-HPLC (HC-A) to give the title compound. 1H NMR (400 MHz, ACETONITRILE-d3 with about 5 μL TFA) δ ppm 9.45 (br. s., 1H), 8.08 (s, 1H), 7.79 (d, J=8.60 Hz, 1H), 7.75 (dd, J=1.30, 8.60 Hz, 1H), 7.25 (dd, J=2.80, 3.00 Hz, 1H), 7.02 (s, 1H), 6.76 (s, 1H), 6.62 (dd, J=2.02, 3.03 Hz, 1H), 4.80 (d, J=10.86 Hz, 1H), 4.63 (d, J=10.86 Hz, 1H), 3.56-3.73 (m, 2H), 2.48 (s, 3H), 1.13 (t, J=6.95 Hz, 3H). HRMS calcd. for C21H20N4O2 (M+H)+ 361.1665. found 361.1658.

Workup

filtrationfiltered through SiO2
washThe SiO2 cake was washed with a mixture of CH2Cl2/MeOH (c.a. 6/1)
concentrationThe organic solution was concentrated
custompurified by RP-HPLC (HC-A)

Sources & evidence

ORD record: ord-8f0c9407e0be49849391905c605ce2ac
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056874B2

Reaction notes

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