Sodium Hydroxide → HCID 66576842, compound

HRID 1409416Notes

Reaction equation

[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:12]2[CH:16]=[CH:15][N:14]([CH2:17][C@@H:18]([NH:20][C:21]([C:23]3[N:24]=[C:25]([CH3:28])[NH:26][CH:27]=3)=[O:22])[CH3:19])[N:13]=2)[CH:7]=[CH:8][C:9]=1[C:10]#[N:11].Br[CH2:30][CH2:31][C:32]#[N:33]>CN(C=O)C>[Cl:3][C:4]1[CH:5]=[C:6]([C:12]2[CH:16]=[CH:15][N:14]([CH2:17][C@@H:18]([NH:20][C:21]([C:23]3[N:24]=[C:25]([CH3:28])[N:26]([CH2:30][CH2:31][C:32]#[N:33])[CH:27]=3)=[O:22])[CH3:19])[N:13]=2)[CH:7]=[CH:8][C:9]=1[C:10]#[N:11]

Participants

Conditions

Temperature: 10 °C

Procedure

Sodium hydroxide, 5 M (1.085 mmol, 0.217 ml) and (S)—N-(1-(3-(3-chloro-4-cyano-phenyl)-1H-pyrazol-1-yl)propan-2-yl)-2-methyl-1H-imidazole-4-carboxamide (0.542 mmol, 200 mg) were dissolved in DMF (2 ml). The mixture was cooled to ˜10° C. with an ice bath and 3-bromopropionitrile (0.813 mmol, 109 mg) was slowly added. The reaction mixture was allowed to warm to RT and it was stirred overnight. The liquids were, evaporated. DCM was added and washed twice with water. The separated organic phase was dried, filtered and evaporated. The crude product was purified by flash chromatography and preparative HPLC, respectively. 73.1 mg of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.07 (d, 3H), 2.38 (s, 3H), 3.02 (t, 2H), 4.22 (t, 2H), 4.24-4.47 (m, 3H), 6.95 (d, 1H), 7.61 (s, 1H), 7.83 (d, 1H), 7.96-8.02 (m, 2H), 8.07-8.13 (m, 2H).

Workup

temperatureto warm to RT
customevaporated
additionDCM was added
washwashed twice with water
customThe separated organic phase was dried
filtrationfiltered
customevaporated
customThe crude product was purified by flash chromatography and preparative HPLC

Sources & evidence

ORD record: ord-22d45e5cdd724571810eba5c892a035b
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921378B2

Reaction notes

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