Sodium Hydroxide → HCID 118413231, compound

HRID 929223Notes

Reaction equation

HRID 929223 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[NH:22][C:21]([O:23][C@H:24]3[C@H:28]4[O:29][CH2:30][CH:31]([CH2:32][C:33]([O:35]CC)=[O:34])[C@H:27]4[O:26][CH2:25]3)=[N:20][C:5]2=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=1.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[NH:22][C:21]([O:23][C@H:24]3[C@H:28]4[O:29][CH2:30][CH:31]([CH2:32][C:33]([OH:35])=[O:34])[C@H:27]4[O:26][CH2:25]3)=[N:20][C:5]2=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 90042283HCID 90042283, compound

Product 1

HCID 118413231HCID 118413231, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture ethyl 2-[(3aR,6R,6aS)-6-[[6-chloro-5-(4-phenylphenyl)-1H-imidazo[4,5-b]pyridin-2-yl]oxy]-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl]acetate (4.4 mg, 0.0085 mmol) and 3M sodium hydroxide (2.8 uL, 0.085 mmol) in ethanol (0.5 ml) was stirred at room temperature for 20 minutes. The reaction mixture was then purified by preparative HPLC reverse phase (C-18), using a 30×150 mm Sunfire™ column and eluting with a 20%-80% acetonitrile/water to give a major and minor isomers which were lyophilized to give the title compounds. Minor isomer: LC-MS: calculated for C26H22ClN3O5 491.12 observed m/e: 492.22 (M+H)+ (Rt 1.11/2 min); 1H NMR δ (ppm) (CD3OD): 7.88 (s, 1H), 7.75 (ABq, 4H), 7.71 (d, 2H), 7.48 (dd, 2H), 7.38 (dd, 1H), 5.56 (qt, 1H), 4.98 (t, 1H), 4.42 (d, 1H), 4.13 (dd, 2H), 4.05-3.98 (m, 3H), 3.72 (dd, 1H), 2.71 (m, 1H) and 2.44-2.33 (m, 2H). Major isomer: LC-MS: calculated for C26H22ClN3O5 491.12 observed m/e: 492.20 (M+H)+ (Rt 1.12/2 min); 1H NMR δ (ppm) (CD3OD): 7.94 (s, 1H), 7.76 (ABq, 4H), 7.72 (d, 2H), 7.49 (dd, 2H), 7.39 (dd, 1H), 5.59 (m, 1H), 5.01 (t, 1H), 4.61 (t, 1H), 4.12 (dd, 2H), 4.08-4.00 (m, 3H), 3.53 (dd, 1H), 2.70 (dd, 1H), 2.59 (m, 1H) and 2.49 (dd, 1H).

Workup

  1. customThe reaction mixture was then purified by preparative HPLC reverse phase (C-18)
  2. washeluting with a 20%-80% acetonitrile/water
  3. customto give a major and minor isomers which

Sources & evidence

ORD record
ord-56a283ce2af041708bbf7db4e48b97e6
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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