Potassium Carbonate → HCID 118049776, compound

HRID 595868Notes

Reaction equation

[CH2:1]([NH:8][C:9](=[O:40])[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:21]([NH:22]C(=O)C(C)(C)C)=[N:20][CH:19]=[C:18]([C@@H:29]3[CH2:34][CH2:33][CH2:32][C@@H:31]([S:35]([CH3:38])(=[O:37])=[O:36])[CH2:30]3)[N:17]=2)=[CH:12][C:11]=1[F:39])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[NH2:22][C:21]1[C:16]([C:13]2[CH:14]=[CH:15][C:10]([C:9]([NH:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:40])=[C:11]([F:39])[CH:12]=2)=[N:17][C:18]([C@@H:29]2[CH2:34][CH2:33][CH2:32][C@@H:31]([S:35]([CH3:38])(=[O:36])=[O:37])[CH2:30]2)=[CH:19][N:20]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To (+/−)-N-benzyl-2-fluoro-4-(6-((1R,3R)-3-(methylsulfonyl)cyclohexyl)-3-pivalamidopyrazin-2-yl)benzamide (25 mg, 0.044 mmol) in MeOH (221 μL) was added potassium carbonate (61.0 mg, 0.441 mmol). The resulting mixture was heated at 80° C. for 4 h. The reaction mixture was filtered and concentrated. Purified with auto-prep to provide 5.4 mg of (+/−)-4-(3-amino-6-((1R,3R)-3-(methylsulfonyl)cyclohexyl)pyrazin-2-yl)-N-benzyl-2-fluorobenzamide in 20.11% yield. LCMS (m/z): 483.1 (MH+), 0.78 min. 1H NMR (400 MHz, MeOD-d4) δ ppm 8.00-7.81 (m, 2H) 7.76-7.56 (m, 2H) 7.43-7.16 (m, 5H) 4.65-4.55 (m, 2H) 3.61-3.51 (m, 1H), 3.46-3.36 (m, 2H) 2.87-2.97 (m, 3H) 2.61-2.48 (m, 1H) 2.19-1.95 (m, 3H) 1.92-1.78 (m, 3H).

Workup

filtrationThe reaction mixture was filtered
concentrationconcentrated
customPurified with auto-prep

Sources & evidence

ORD record: ord-10a41aacd7164eceb386920b7ecc0703
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242996B2

Reaction notes

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