4-Chlorophenyl chloroformate → HCID 25204385, compound

HRID 1895689Notes

Reaction equation

HRID 1895689 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:16]=[CH:15][C:14]([O:17][CH:18]3C[CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])(C)[CH3:28])=[O:25])[CH2:20][CH2:19]3)=[CH:13][C:12]2=[O:31])=[CH:7][CH:6]=1)(=[O:4])=[O:3].ClC(OC1C=[CH:40][C:39]([Cl:42])=[CH:38]C=1)=O.ClC(OC(C)C(F)(F)F)=O>>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH:19]3[CH2:22][N:21]([C:24]([O:26][C:27]4[CH:28]=[CH:40][C:39]([Cl:42])=[CH:38][CH:30]=4)=[O:25])[CH2:20]3)=[CH:13][C:12]2=[O:31])=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

4

Reactant 3

HCID 1390594-Chlorophenyl chloroformateHCID 25204174Tert-butyl 4-(1-(4-(methylsulfonyl)phenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylateHCID 582703481,1,1-Trifluoropropan-2-yl carbonochloridate

Product 1

HCID 25204385HCID 25204385, compound

Procedure

Example 21 was prepared according to procedures described in Example 2, Step A and Step C, substituting tert-butyl 3-((1-(4-(methylsulfonyl)phenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)methyl)azetidine-1-carboxylate for tert-butyl 4-(1-(4-(methylsulfonyl)phenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate in Step A and 4-chlorophenyl chloroformate for 1,1,1-trifluoropropan-2-yl chloroformate in Step C. 1H NMR (500 MHz, CDCl3) δ 8.09 (d, J=8.25 Hz, 2 H), 7.62 (d, J=8.80 Hz, 2 H), 7.29-7.36 (m, 3 H), 7.05-7.12 (m, 2 H), 6.16-6.25 (m, 2 H), 4.38 (app br. s, 1 H), 4.28 (app br. s, 1 H), 4.21 (d, J=6.05 Hz, 2 H), 4.09 (app br. s, 1 H), 4.00 (app br. s, 1 H), 3.14-3.23 (m, 1 H), 3.11 (s, 3 H). MS (ESI) 489 (M+H).

Workup

  1. customExample 21 was prepared

Sources & evidence

ORD record
ord-4c36869081d54278b2d60fd36b4d0db6
Source dataset
uspto-grants-2013_08
Patent number
US08513424B2

Reaction notes

Loading…