(+)-Glycidol → HCID 178488895, compound

HRID 591941Notes

Reaction equation

HRID 591941 reaction equation
[Cl:1][C:2]1[C:3]([NH:25][C@@H:26]2[C@@H:31]3[CH2:32][C@@H:28]([CH:29]=[CH:30]3)[C@@H:27]2[C:33]([NH2:35])=[O:34])=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=3[CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[NH:8][C:5]2=[N:6][CH:7]=1.[O:36]1[CH2:38][C@H:37]1[CH2:39][OH:40]>CO>[Cl:1][C:2]1[C:3]([NH:25][CH:26]2[CH:31]3[CH2:32][CH:28]([CH:29]=[CH:30]3)[CH:27]2[C:33]([NH2:35])=[O:34])=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=3[CH:19]3[CH2:20][CH2:21][N:22]([CH2:38][C@H:37]([OH:36])[CH2:39][OH:40])[CH2:23][CH2:24]3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 5460455(+)-GlycidolHCID 178488908HCID 178488908, compound2×

Product 1

HCID 178488895HCID 178488895, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(1S,2S,3R,4R)-3-[6-Chloro-2-(4-methoxy-2-piperidin-4-yl-phenyl)-3H-imidazo[4,5-b]pyridine-7-ylamino]-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (Compound XXX) (60 mg, 0.1 mmol) was stirred with (R)-1-oxiranyl-methanol (14.0 mg, 1.5 mmol) in methanol (5 mL) in a sealed tube overnight. The reaction was concentrated and the product purified by reverse phase chromatography (Gilson). Desired fractions were collected, combined, and lyophilized to afford the title compound as a white lyophilate (46 mg, 70%). 1H NMR (d-chloroform): 9.16 (br s, 1H), 8.03 (s, 1H), 7.65 (m, 2H), 7.30 (m, 1H), 7.02 (d, J=9 Hz, 1H), 6.95 (s, 1H), 6.32 (s, 1H), 6.17 (s, 1H), 5.52 (br m, 1H), 5.15 (m, 1H), 3.87 (m, 1H), 3.85 (s, 3H), 3.65-3.26 (m, 8H), 3.22-2.70 (m, 5H), 2.24 (d, J=9 Hz, 1H), 2.12 (m, 4H), 1.94 (m, 1H), 1.28 (s, 1H), 1.18 (d, J=5 Hz, 3H). MS: 567.17 (M+H). HPLC retention time: 1.91 minutes (G Method).

Workup

  1. concentrationThe reaction was concentrated
  2. customthe product purified by reverse phase chromatography (Gilson)
  3. customDesired fractions were collected

Sources & evidence

ORD record
ord-20fb59c5cb6443e6ba4ecff42d88c1bd
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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