HCID 118235427, compound → HCID 118235457, compound

HRID 626987Notes

Reaction equation

HRID 626987 reaction equation
[F:1][CH:2]([F:39])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]1[N:15]2[CH:16]=[C:17]([C:21]3[CH:22]=[N:23][C:24]([C:27]4[CH2:32][CH2:31][CH:30]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:29][CH:28]=4)=[N:25][CH:26]=3)[C:18]([F:20])=[CH:19][C:14]2=[N:13][C:12]=1[CH3:38]>C(O)C>[F:39][CH:2]([F:1])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]1[N:15]2[CH:16]=[C:17]([C:21]3[CH:22]=[N:23][C:24]([CH:27]4[CH2:28][CH2:29][CH:30]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:31][CH2:32]4)=[N:25][CH:26]=3)[C:18]([F:20])=[CH:19][C:14]2=[N:13][C:12]=1[CH3:38]

Participants

3

Reactant 1

HCID 118235427HCID 118235427, compound

Product 1

HCID 118235457HCID 118235457, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of Example 163 (˜0.05M, 545 mg, 1.01 mmol) in ethanol was hydrogenated using an H-Cube® (ThalesNano) at a flow rate of 0.5 mL/minute, in full H2 mode (1 bar) at 50° C. Removal of the ethanol under vacuum gave the title compound (545 mg, 89%) as a pale brown foam consisting of a pair diastereosiomers in a 3:1 ratio. δH (300 MHz, CD3OD) 8.76 (s, 2H), 8.24 (d, J 7.4 Hz, 1H), 7.25 (m, 2H), 7.07 (m, 3H), 6.81 (t, J 74.1 Hz, 1H), 4.32 (s, 2H), 4.09 (2H, qd, J 7.3, 1.2 Hz), 2.97 (m, 1H), 2.64 (m, 1H), 2.33 (m, 1H), 1.83 (m, 8H), 1.21 (t, J 7.1 Hz, 3H). LC-MS (pH 3): MH+ m/z 539.8, RT 2.46 minutes; 539.8, RT 2.51 minutes. LC-MS (pH 10): MH+ m/z 539.8, RT 2.47 minutes; 539.8, RT 2.51 minutes.

Workup

  1. customat 50° C
  2. customRemoval of the ethanol under vacuum

Sources & evidence

ORD record
ord-0c94addee0ac4dfe8563f420e803058e
Source dataset
uspto-grants-2016_04
Patent number
US09309243B2

Reaction notes

Loading…