Potassium Carbonate → HCID 90408137, compound

HRID 594083Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)=[CH:4][C:3]=1[C:21]1[N:22]=[C:23]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[C:24](=[O:27])[NH:25][CH:26]=1.[F:34][CH:35]([F:38])[CH2:36]I.C(=O)([O-])[O-].[K+].[K+]>>[F:34][CH:35]([F:38])[CH2:36][N:25]1[C:24](=[O:27])[C:23]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[N:22][C:21]([C:3]2[CH:4]=[C:5]([NH:8][C:9](=[O:20])[C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:17])([F:19])[F:18])[CH:11]=3)[CH:6]=[CH:7][C:2]=2[CH3:1])=[CH:26]1

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 38335651,1-Difluoro-2-iodoethane

HCID 86298304HCID 86298304, compound

Product 1

HCID 90408137HCID 90408137, compound

Procedure

Method 1 was followed using N-(4-methyl-3-(6-morpholino-5-oxo-4,5-dihydropyrazin-2-yl)phenyl)-3-(trifluoromethyl)benzamide (1.0 equiv.), 1,1-difluoro-2-iodoethane (1.2 equiv.) and potassium carbonate (2.0 equiv.) at 60° C. 1H NMR (400 MHz, <cd3od>) δ ppm 2.39 (s, 3H) 3.81 (d, J=5.09 Hz, 8H) 4.38 (td, J=14.09, 3.91 Hz, 2H) 6.02-6.44 (m, 1H) 7.14 (s, 1H) 7.26 (d, J=8.22 Hz, 1H) 7.59 (dd, J=8.22, 1.96 Hz, 1H) 7.67-7.79 (m, 2H) 7.89 (d, J=7.83 Hz, 1H) 8.16-8.34 (m, 1H). LCMS (m/z) (M+H)=523.3, Rt=1.05 min.

Workup

customat 60° C

Sources & evidence

ORD record: ord-9ea50a2e00154c62bf934e554fa64bc9
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242969B2

Reaction notes

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