Isoamylamine → HCID 178422423, compound

HRID 2174058Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH3:24])[C:5]([C:21]#[C:22]Br)=[C:6]2[C:10]=1[N:9](S(C1C=CC(C)=CC=1)(=O)=O)[CH:8]=[CH:7]2.[NH2:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[NH2:34])[C:29]#[N:30].C1N2CCN(CC2)C1.[OH-].[K+].C(N)CC(C)C>CN1C(=O)CCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH3:24])[C:5]([CH2:21][C:22]2[NH:34][C:33]3[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][C:26]=3[N:25]=2)=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 7-bromo-4-(bromoethynyl)-5-methyl-1-tosyl-1H-indole (35 mg, 0.075 mmol) and 3,4-diaminobenzonitrile (14.96 mg, 0.112 mmol) and DABCO (10.08 mg, 0.090 mmol) in NMP (0.3 mL) was stirred at 100° C. After stirring overnight the reaction mixture was loaded onto silica gel and was purified by flash chromatography (0-100% EtOAc in heptanes). The resulting residue was dissolved in EtOH (1.1 mL), KOH (51.8 mg, 0.924 mmol) and isoamylamine (0.21 mL, 1.85 mmol) were added, and the mixture was heated at 100° C. using microwave irradiation for 40 minutes. The resulting residue was purified directly by RP-HPLC (HC-A) to provide the title compound. 1H NMR (TFA salt, 400 MHz, DMSO-d6) δ ppm 11.22 (br. s., 1H) 7.97 (s, 1H) 7.59 (d, J=7.83 Hz, 1H) 7.51 (dd, J=8.21, 1.39 Hz, 1H) 7.33 (t, J=2.91 Hz, 1H) 7.21 (s, 1H) 6.55-6.66 (m, 1H) 4.47 (s, 2H) 2.38 (s, 3H). HRMS calcd. for C18H13BrN4 (M+H)+ 365.0396. found 365.0408.

Workup

customwas purified by flash chromatography (0-100% EtOAc in heptanes)
dissolutionThe resulting residue was dissolved in EtOH (1.1 mL)
custommicrowave irradiation for 40 minutes
customThe resulting residue was purified directly by RP-HPLC (HC-A)

Sources & evidence

ORD record: ord-18887146b6574926b56996eb826bd06b
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056874B2

Reaction notes

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