Ammonia → HCID 71556667, compound

HRID 709514Notes

Reaction equation

HRID 709514 reaction equation
[OH:1][C@H:2]([C@@H:8]([OH:35])[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][N:26]=3)=[CH:20][CH:19]=2)[CH:10]=1)[C:3]([O:5]CC)=O.[NH3:36]>>[OH:1][C@H:2]([C@@H:8]([OH:35])[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:33])([F:32])[F:34])=[CH:27][N:26]=3)=[CH:20][CH:19]=2)[CH:10]=1)[C:3]([NH2:36])=[O:5]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 89545437HCID 89545437, compound

Product 1

HCID 71556667HCID 71556667, compound

Procedure

(2R,3S)-2,3-Dihydroxy-3-(1-(4-((5-(trifluoromethyl)pyridin-2-yl)oxy)phenyl)-1H-indol-3-yl)propanamide (5) was prepared as follows: A solution of compound 4 (100 mg) and NH3 (in MeOH ˜7N, 6 mL) was shaken at room temperature for 72 hours. The solvent was evaporated, and the residue was purified by column (EtOAc/MeOH 8/1.5) to afford compound 5 as a white solid (70 mg): 1H-NMR (400 MHz, CD3OD) δ: 8.49 (s, 1H), 8.06 (1H, dd, 2.6 & 8.7 Hz), 7.82 (1H, d, 7.8 Hz), 7.56-7.65 (m, 4H), 7.38-7.41 (m, 2H), 7.15-7.25 (m, 3H), 5.51 (dd, 1H, 0.8 & 2.6 Hz), 4.37 (1H, d, 2.6 Hz); LC/MS: m/z=480.2 [M+Na+] (Calc: 457.4).

Workup

  1. custom(2R,3S)-2,3-Dihydroxy-3-(1-(4-((5-(trifluoromethyl)pyridin-2-yl)oxy)phenyl)-1H-indol-3-yl)propanamide (5) was prepared
  2. customThe solvent was evaporated
  3. customthe residue was purified by column (EtOAc/MeOH 8/1.5)

Sources & evidence

ORD record
ord-6942618a6c40477d93e36fdeda318eff
Source dataset
uspto-grants-2015_11
Patent number
US09181185B2

Reaction notes

Loading…