m-Toluidine → HCID 86584498, compound

HRID 1264639Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].CS[C:11](=[C:14]([C:17]#[N:18])[C:15]#[N:16])SC.[NH2:19][C@H:20]1[CH2:26][CH2:25][CH2:24][CH2:23][N:22]([CH2:27][C:28]([N:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)=[O:29])[C:21]1=[O:35]>C(O)C>[C:15]([C:14]([C:17]#[N:18])=[C:11]([NH:19][C@H:20]1[CH2:26][CH2:25][CH2:24][CH2:23][N:22]([CH2:27][C:28]([N:30]2[CH2:31][CH2:32][CH2:33][CH2:34]2)=[O:29])[C:21]1=[O:35])[NH:5][C:4]1[CH:6]=[CH:7][CH:8]=[C:2]([CH3:1])[CH:3]=1)#[N:16]

Participants

Conditions

Temperature: 80 °C

Procedure

3-Methylaniline (32.2 mg, 0.250 mmol) and [bis (methylthio)methylene]propanedinitrile (35.5 mg, 0.209 mmol) were dissolved in ethanol(0.3 mL). The reaction mixture was heated at 80° C. for 3 h. To the mixture was added 1-[[(3S) -3-aminohexahydro-2-oxo-1H-azepin-1-yl]acetyl]pyrrolidine (50.0 mg, 0.209 mmol) and the reaction mixture was heated at 80° C. for another 40 h. Purification by preparative RP HPLC provided the title compound as a pale yellow solid (22 mg, 45%): MS (ESI, pos. ion spectrum) m/z 421; HPLC (method A) tR 3.39 min.

Workup

temperaturethe reaction mixture was heated at 80° C. for another 40 h
customPurification by preparative RP HPLC

Sources & evidence

ORD record: ord-7c4f299383e54515bd78901a53d39168
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06544981B2

Reaction notes

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