Dichloromethane → HCID 70656195, compound

HRID 872733Notes

Reaction equation

[NH:1]1[CH:5]=[C:4]([C:6](=[S:8])[NH2:7])[CH:3]=[N:2]1.Br[CH2:10][C:11](=O)[C:12]([OH:14])=O.[NH2:16][C@H:17]([CH3:33])[CH2:18][N:19]1[CH:23]=[CH:22][C:21]([C:24]2[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[C:26]([Cl:32])[CH:25]=2)=[N:20]1.C(Cl)Cl>C1COCC1>[Cl:32][C:26]1[CH:25]=[C:24]([C:21]2[CH:22]=[CH:23][N:19]([CH2:18][C@H:17]([NH:16][C:12]([C:11]3[N:7]=[C:6]([C:4]4[CH:5]=[N:1][NH:2][CH:3]=4)[S:8][CH:10]=3)=[O:14])[CH3:33])[N:20]=2)[CH:31]=[CH:30][C:27]=1[C:28]#[N:29]

Participants

Conditions

Temperature: 60 °C

Procedure

1H-Pyrazole-4-carbothioic acid amide (300 mg, 2.359 mmol) and 3-bromo-2-oxopropanoic acid (433 mg, 2.60 mmol) were dissolved in dry THF under nitrogen atmosphere. The reaction mixture was heated at 60° C. for 3 h. The reaction mixture was cooled to RT and evaporated to dryness. (R)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (300 mg, 1.151 mmol) and DCM were added to the reaction flask and the title compound was prepared using the method of Example 34(d). The product was purified by Flash-chromatography and triturated using methanol. Yield 13.7%. 1H-NMR (400 MHz; DMSO): δ 1.17 (d, 3H), 4.31-4.54 (m, 3H), 6.96 (d, 1H), 7.84 (d, 1H), 7.87 (d, 1H), 7.94 (dd, 1H), 8.00 (bs, 1H), 8.06 (d, 1H), 8.08 (d, 1H), 8.38 (d, 1H), 8.40 (bs, 1H), 13.38 (s, 1H).

Workup

temperatureThe reaction mixture was cooled to RT
customevaporated to dryness
customThe product was purified by Flash-chromatography
customtriturated

Sources & evidence

ORD record: ord-f6dee10311364ed8b70b8001735e9bc6
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975254B2

Reaction notes

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