(R)-1,2-Epoxypropane → HCID 178491974, compound

HRID 591948Notes

Reaction equation

HRID 591948 reaction equation
[Cl:1][C:2]1[C:3]([NH:26][C@@H:27]2[C@@H:32]3[CH2:33][C@@H:29]([CH:30]=[CH:31]3)[C@@H:28]2[C:34]([NH2:36])=[O:35])=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH2:17][N:18]4[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]4)=[CH:13][C:12]=3[O:24][CH3:25])[NH:8][C:5]2=[N:6][CH:7]=1.[CH2:37]1[O:40][C@@H:38]1[CH3:39]>>[Cl:1][C:2]1[C:3]([NH:26][C@@H:27]2[C@@H:32]3[CH2:33][C@@H:29]([CH:30]=[CH:31]3)[C@@H:28]2[C:34]([NH2:36])=[O:35])=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH2:17][N:18]4[CH2:23][CH2:22][N:21]([CH2:37][C@H:38]([OH:40])[CH3:39])[CH2:20][CH2:19]4)=[CH:13][C:12]=3[O:24][CH3:25])[NH:8][C:5]2=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 146261(R)-1,2-EpoxypropaneHCID 178491965HCID 178491965, compound

Product 1

HCID 178491974HCID 178491974, compoundYield 32%

Procedure

In a similar fashion as for the synthesis of Compound XLIII, (1S,2S,3R,4R)-3-[6-Chloro-2-(2-methoxy-4-piperazin-1-ylmethyl-phenyl)-3H-imidazo[4,5-b]pyridine-7-ylamino]-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide was reacted with (R)-(−)-propylene oxide to afford the title compound as an orange solid (32%). Mp 157-9° C. 1H NMR (d-chloroform): 10.72 (br s, 1H), 8.35 (d, J=9 Hz, 1H), 8.05 (s, 1H), 7.04 (m, 2H), 6.37 (m, 3H), 5.56 (d, J=9 Hz, 1H), 5.20 (t, J=8 Hz, 1H), 5.12 (s, 1H), 4.08 (s, 3H), 3.84 (m, 1H), 3.59 (s, 2H), 3.48 (m, 1H), 3.18 (s, 1H), 2.92 (s 1H), 2.88 (d, J=8 Hz, 1H), 2.73 (m, 2H), 2.61-2.41 (m, 5H), 2.37-2.22 (m, 3H), 2.19 (s, 1H), 1.76 (d, J=9 Hz, 1H), 1.15 (d, J=7 Hz, 3H). MS: 566.23 (M+H). HPLC retention time: 1.71 minutes (G Method).

Sources & evidence

ORD record
ord-292798db485241989267f5ae4cad9948
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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