HCID 66741798, compound → HCID 66741637, compound

HRID 541019Notes

Reaction equation

HRID 541019 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[C:10]([Cl:38])[C:11]([NH:18][CH2:19][CH:20]([OH:37])[CH2:21][O:22][CH:23]3[CH2:26][N:25](C(OCC4C=CC=CC=4)=O)[CH2:24]3)=[C:12]([F:17])[CH:13]=2)[N:8]([C:39]2[C:44]([F:45])=[CH:43][C:42]([F:46])=[C:41]([NH2:47])[N:40]=2)[CH:7]=1)=[O:5])[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[C:10]([Cl:38])[C:11]([NH:18][CH2:19][CH:20]([OH:37])[CH2:21][O:22][CH:23]3[CH2:26][NH:25][CH2:24]3)=[C:12]([F:17])[CH:13]=2)[N:8]([C:39]2[C:44]([F:45])=[CH:43][C:42]([F:46])=[C:41]([NH2:47])[N:40]=2)[CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 66741798HCID 66741798, compound

Product 1

HCID 66741637HCID 66741637, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To a slurry of 10% Pd on carbon (2.1 g) in MeOH (20 mL) was added a solution of 11 (13.7 g, 20.3 mmol) in MeOH (230 mL). The mixture was hydrogenated at 1 atm. for 1 h, filtered over Hyflo and evaporated yielding 12 as beige crystals (10.3 g, 93%). Mp. 148-152° C.; 1H NMR (300 MHz, DMSO-d6): δ 1.27 (3H, t, J=7.1 Hz), 3.27 (1H, d, J=5.0 Hz), 3.28-3.80 (10H, m), 4.19 (1H, br. s), 4.21 (2H, q, J=7.1 Hz), 5.86 (1H, s), 6.74 (2H, s), 7.84 (1H, d, J=13.8 Hz), 7.94 (1H, dd, J=9.7, 9.0 Hz), 8.43 (1H, s); 13C NMR (75 MHz, CDCl3): δ 14.1, 48.4 (d, JF=10 Hz), 53.6, 60.2, 68.4, 70.4 (d, JF=4 Hz), 72.1, 106.4 (d, JF=6 Hz), 111.0, 111.3 (d, JF=23 Hz), 113.6 (dd, JF=23, 21 Hz), 118.9 (d, JF=6 Hz), 133.8 (d, JF=13 Hz), 134.2, 139.5 (d, JF=12 Hz), 143.3 (dd, JF=248, 4 Hz), 145.0 (dd, JF=259, 5 Hz), 145.6 (d, JF=14 Hz), 149.3 (d, JF=245 Hz), 149.5, 163.5, 171.0; IR: (KBr) 1697, 1614, 1496, 1457 cm−1; ES-HRMS m/z: (M++1H) calcd. for C23H24ClF3N5O5 542.1413. found 542.1391.

Workup

  1. filtrationfiltered over Hyflo
  2. customevaporated

Sources & evidence

ORD record
ord-02a261047a864decb3a828abb8380d75
Source dataset
uspto-grants-2014_10
Patent number
US08871938B2

Reaction notes

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