Hydrochloric Acid → HCID 11516750, compound

HRID 2426811Notes

Reaction equation

Cl.Cl[C:3]1[CH:8]=[C:7]([C:9]2[O:13][C:12]([C@@:14]([NH:23]C(=O)OC(C)(C)C)([CH3:22])CC3C=CC=CC=3)=[N:11][N:10]=2)[CH:6]=[C:5]([N:31]([CH3:36])[S:32]([CH3:35])(=[O:34])=[O:33])[N:4]=1.CCO[C:40]([CH3:42])=O>>[NH2:23][CH:14]([C:12]1[O:13][C:9]([C:7]2[CH:8]=[C:3]([N:4]([CH3:5])[CH2:3][CH:8]3[CH2:7][CH:40]3[CH3:42])[N:4]=[C:5]([N:31]([CH3:36])[S:32]([CH3:35])(=[O:33])=[O:34])[CH:6]=2)=[N:10][N:11]=1)[CH3:22]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 8857Ethyl Acetate

HCID 59028325HCID 59028325, compound

Product 1

HCID 11516750HCID 11516750, compound

Procedure

HCl was bubbled through a solution of product from Step B (0.532 g, 1.08 mmol) in 15 mL EtOAc at 0° C. for 5 min. The bright yellow solution was warmed to rt for 1 h, then concentrated to afford N-(4-[5-(1-aminoethyl)-1,3,4-oxadiazol-2-yl]-6-{methyl[(2-methylcyclopropyl)methyl]amino}pyridin-2-yl)-N-methylmethanesulfonamide as a yellow foam which was used without further purification. 1H NMR (d4-MeOH, 400 MHz) δ 7.15 (s, 1H), 7.05 (s, 1H), 4.95 (q, J=7.0 Hz, 1H), 3.61 (dd, J=14.5, 8.1 Hz, 1H), 3.43 (dd, J=14.5, 6.9 Hz, 1H), 3.38 (s, 3H), 3.16 (s, 3H), 3.15 (s, 3H), 1.79 (d, J=7.0 Hz, 3H), 1.01 (d, J=5.8 Hz, 3H), 0.82-0.75 (m, 2H), 0.47 (m, 1H), 0.25 (m, 1H); LCMS [M+H]+=395.

Workup

concentrationconcentrated

Sources & evidence

ORD record: ord-e0b57be8e876444c8bfe27ef717148e0
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968571B2

Reaction notes

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