Hydrochloric Acid → Cyclohexylmethyl-[6-(2-[1,3,4]oxadiazol-2-yl-pyridin-4-yloxy)-benzooxazol-2-yl]-amine

HRID 2370504Notes

Reaction equation

HRID 2370504 reaction equation
[CH:1]1([CH2:7][NH:8][C:9]2[O:10][C:11]3[CH:17]=[C:16]([O:18][C:19]4[CH:24]=[CH:23][N:22]=[C:21]([C:25]([NH:27][NH2:28])=[O:26])[CH:20]=4)[CH:15]=[CH:14][C:12]=3[N:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[CH:30](OC)(OC)OC>>[CH:1]1([CH2:7][NH:8][C:9]2[O:10][C:11]3[CH:17]=[C:16]([O:18][C:19]4[CH:24]=[CH:23][N:22]=[C:21]([C:25]5[O:26][CH:30]=[N:28][N:27]=5)[CH:20]=4)[CH:15]=[CH:14][C:12]=3[N:13]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 9005Trimethyl orthoformateHCID 577254564-(2-(Cyclohexylmethylamino)benzo[d]oxazol-6-yloxy)pyridine-2-carbohydrazide

Product 1

HCID 24821148Cyclohexylmethyl-[6-(2-[1,3,4]oxadiazol-2-yl-pyridin-4-yloxy)-benzooxazol-2-yl]-amine

Procedure

A solution of 4-(2-(cyclohexylmethylamino)benzo[d]oxazol-6-yloxy)pyridine-2-carbohydrazide (8 mg, 0.019 mmol, 1.0 eq) and 0.1 mL of 4 M hydrogen chloride in 1 mL trimethyl orthoformate was heated in the microwave at 120° C. for 1200 seconds. The crude product was purified by reverse phase prep HPLC to give the title compound. MH+=392.0

Workup

  1. customThe crude product was purified by reverse phase prep HPLC

Sources & evidence

ORD record
ord-d268a1407da84863bf8edcc6c6db46e2
Source dataset
uspto-grants-2014_04
Patent number
US08710048B2

Reaction notes

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