2-Chlorobenzoxazole → HCID 178481619, compound

HRID 707360Notes

Reaction equation

HRID 707360 reaction equation
C(OC(=O)N[C@H]1C[C@H](NC2SC3C=CC=CC=3N=2)C1)(C)(C)C.Cl.Cl.[NH2:25][C@H:26]1[CH2:29][C@H:28]([N:30]2[C:34]3=[N:35][CH:36]=[CH:37][CH:38]=[C:33]3[N:32]([CH3:39])[C:31]2=[O:40])[CH2:27]1.C(N(C(C)C)CC)(C)C.Cl[C:51]1[O:52][C:53]2[CH:59]=[CH:58][CH:57]=[CH:56][C:54]=2[N:55]=1>CN(C)C1C=CN=CC=1.CS(C)=O>[O:52]1[C:53]2[CH:59]=[CH:58][CH:57]=[CH:56][C:54]=2[N:55]=[C:51]1[NH:25][C@H:26]1[CH2:29][C@H:28]([N:30]2[C:34]3=[N:35][CH:36]=[CH:37][CH:38]=[C:33]3[N:32]([CH3:39])[C:31]2=[O:40])[CH2:27]1

Participants

7

Reactant 4

HCID 119862-ChlorobenzoxazoleHCID 81531DiisopropylethylamineHCID 178454113HCID 178454113, compoundHCID 178478634HCID 178478634, compound

Product 1

HCID 178481619HCID 178481619, compoundYield 60.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound was synthesized following the procedure described for INTERMEDIATE 10, using 3-(trans-3-aminocyclobutyl)-1-methyl-1H-imidazo[4,5-b]pyridin-2(3H)-one dihydrochloride (0.146 g, 0.501 mmol), diisopropylethylamine (1 ml, 5.75 mmol), 4-dimethylaminopyridine (6.13 mg, 0.050 mmol), and 2-chlorobenzoxazole (0.057 ml, 0.501 mmol) in DMSO (0.5 mL) to afford 3-(trans-3-(benzo[d]oxazol-2-ylamino)cyclobutyl)-1-methyl-1H-imidazo[4,5-b]pyridin-2(3H)-one (0.102 g, 0.304 mmol, 60.7% yield). m/z: 336.2 (M+1); 1H NMR (400 MHz, DMSO-dh) δ: ppm 8.44 (d, J=5.87 Hz, 1 H), 8.04 (d, J=4.69 Hz, 1 H), 7.50 (d, J=7.43 Hz, 1 H), 7.37 (d, J=7.82 Hz, 1 H), 7.28 (d, J=7.63 Hz, 1 H), 7.05-7.19 (m, 2 H), 6.92-7.03 (m, 1 H), 5.26 (t, J=8.22 Hz, 1 H), 4.53 (br. s., 1 H), 3.23-3.46 (m, 5 H), 2.38-2.61 (m, 2 H).

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-fca4607f51914ff1a9bbe06626aa60a9
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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