Diisopropylethylamine → HCID 89907899, compound

HRID 924037Notes

Reaction equation

[Br:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([S:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[NH:23]1[CH2:27][CH2:26][C@H:25]([OH:28])[CH2:24]1.CCN(C(C)C)C(C)C>CC(O)C>[Br:1][C:2]1[C:3]([N:23]2[CH2:27][CH2:26][C@H:25]([OH:28])[CH2:24]2)=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([S:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8]

Participants

Conditions

Temperature: 140 °C

Procedure

5-Bromo-6-chloro-N-(4-((trifluoromethyl)thio)phenyl)nicotinamide (Stage 185.2, 206 mg, 0.5 mmol) and (S)-pyrrolidin-3-ol (52.3 mg, 0.6 mmol) were dissolved in iPrOH (0.5 mL). DIPEA (192 μL, 1.1 mmol) was added and the RM mixture was heated at 140° C. for 1 h in a pressure safe vial. The vial was cooled to RT and the RM was evaporated to dryness under reduced pressure to give residue that was purified by flash chromatography (RediSep® Silica gel column, n-heptane/EtOAc, from 20% to 100% EtOAc). Trituration with n-heptane, filtered and dried afforded the title compound as a white crystalline powder. HPLC (Condition 4) tR=5.89 min, UPLC-MS (Condition 3) tR=1.20 min, m/z=464.1 [M+H]+.

Workup

temperatureThe vial was cooled to RT
customthe RM was evaporated to dryness under reduced pressure
customto give residue that
customwas purified by flash chromatography (RediSep® Silica gel column, n-heptane/EtOAc, from 20% to 100% EtOAc)
filtrationTrituration with n-heptane, filtered
customdried

Sources & evidence

ORD record: ord-e24dd67c482d4a9da5f5af8142c6b7ab
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278981B2

Reaction notes

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