4-Fluorobenzoyl isothiocyanate → HCID 178501176, compound

HRID 518617Notes

Reaction equation

[NH2:1][C:2]1[C:3]([NH:17][C@@H:18]2[CH2:23][CH2:22][C@H:21]([C:24]([O:26][CH3:27])=[O:25])[CH2:20][CH2:19]2)=[CH:4][C:5]([O:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[N:6][CH:7]=1.[F:28][C:29]1[CH:39]=[CH:38][C:32]([C:33]([N:35]=[C:36]=S)=[O:34])=[CH:31][CH:30]=1>>[F:28][C:29]1[CH:30]=[CH:31][C:32]([C:33](/[N:35]=[C:36]2/[N:17]([C@@H:18]3[CH2:19][CH2:20][C@H:21]([C:24]([O:26][CH3:27])=[O:25])[CH2:22][CH2:23]3)[C:3]3[CH:4]=[C:5]([O:8][CH2:9][CH2:10][N:11]4[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]4)[N:6]=[CH:7][C:2]=3[NH:1]/2)=[O:34])=[CH:38][CH:39]=1.[C:33](/[N:35]=[C:36]1/[N:17]([C@@H:18]2[CH2:19][CH2:20][C@H:21]([C:24]([O:26][CH3:27])=[O:25])[CH2:22][CH2:23]2)[C:3]2[CH:4]=[CH:5][N:6]=[CH:7][C:2]=2[NH:1]/1)(=[O:34])[C:32]1[CH:38]=[CH:39][CH:29]=[CH:30][CH:31]=1

Participants

Reactant 2

HCID 2490894-Fluorobenzoyl isothiocyanate

HCID 178501202HCID 178501202, compound

Product 2

HCID 178501176HCID 178501176, compoundYield 55.3%

HCID 178501187HCID 178501187, compound

Procedure

The title compound was prepared from cis-methyl 4-(5-amino-2-(2-(piperidin-1-yl)ethoxy)pyridin-4-ylamino)cyclohexanecarboxylate and 4-fluorobenzoyl isothiocyanate using a method analogous to the preparation of cis-methyl 4-((E)-2-(benzoylimino)-2,3-dihydro-1H-imidazo[4,5-c]pyridin-1-yl)cyclohexanecarboxylate (100 mg, 55.3% yield). MS m/z=524.2 [M+H]. Calc'd for C28H34FN5O4: 523.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.19-1.30 (m, 2H) 1.34-1.45 (m, 2H) 1.46-1.60 (m, 4H) 1.66-1.91 (m, 5H) 2.17-2.27 (m, 2H) 2.35-2.49 (m, 3H) 2.53-2.62 (m, 2H) 2.78-2.90 (m, 1H) 3.75 (s, 3H) 4.29-4.46 (m, 2H) 4.55-4.70 (m, 1H) 6.94 (s, 1H) 7.23-7.36 (m, 2H) 8.19-8.31 (m, 3H) 12.70 (s, 1H).

Sources & evidence

ORD record: ord-15b2a1fb6b144e4b9d1a6573d0ca5eb7
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115127B2

Reaction notes

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