Isopropanol → HCID 118198934, compound

HRID 923917Notes

Reaction equation

HRID 923917 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]([O: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]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:24]1.CC(O)C.CCN(C(C)C)C(C)C>O>[Br:1][C:2]1[C:3]([N:23]2[CH2:27][CH2:26][C@@H:25]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:33])([CH3:32])[CH3:34])[CH2:24]2)=[N:4][CH:5]=[C:6]([C:7](=[O:8])[NH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=2)[CH:21]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 81531DiisopropylethylamineHCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 867025955-bromo-6-chloro-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 118198934HCID 118198934, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-bromo-6-chloro-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 12.2, 0.5 g, 1.264 mmol), (R)-tert-butyl pyrrolidin-3-ylcarbamate (283 mg, 1.517 mmol), iPrOH (4 mL) and DIPEA (0.442 mL, 0.327 g, 2.53 mmol) were subjected to MW irradiation at 140° C. for 30 min. The vial was cooled to RT and the RM was added to water (100 mL) and the resulting precipitate was collected by filtration. The obtained solid was washed with water (50 mL) and dried to afford the title compound as an off-white powder. LC-MS (Condition 6) tR=1.47 min, m/z=488.9/490.9 [M+H—H2C═C(CH3)2], m/z=545/547.0 [M+H]+.

Workup

  1. customwere subjected to MW irradiation at 140° C. for 30 min
  2. filtrationthe resulting precipitate was collected by filtration
  3. washThe obtained solid was washed with water (50 mL)
  4. customdried

Sources & evidence

ORD record
ord-7be436bb63474014bc7d5a51e0b90aa3
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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