Dichloromethane → HCID 52920064, compound

HRID 872734Notes

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 (1.0 g, 7.86 mmol) and 3-bromo-2-oxopropanoic acid (1.44 g, 8.65 mmol) were dissolved in dry THF under nitrogen atmosphere. The reaction mixture was heated at 60° C. for 4.5 h. The reaction mixture was cooled to RT and evaporated to dryness. (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (1.367 g, 5.24 mmol) and DCM were added to the reaction flask and the title compound was prepared using the method of Example 34(d). The product purified by Flash-chromatography and triturated using acetonitrile. Yield 37.7%. 1H-NMR (400 MHz; DMSO): δ 1.11 (d, 3H), 4.25-4.48 (m, 3H), 6.89 (d, 1H), 7.77 (d, 1H), 7.80 (d, 1H), 7.87 (dd, 1H), 7.93 (bs, 1H), 7.99 (d, 1H), 8.01 (s, 1H), 8.31 (d, 1H), 8.33 (bs, 1H), 13.31 (bs, 1H).

Workup

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

Sources & evidence

ORD record: ord-815c8d57f2434be4a27c728de25f1cf7
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975254B2

Reaction notes

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