Methyl azetidine-3-carboxylate hydrochloride → HCID 57524621, compound

HRID 2278789Notes

Reaction equation

HRID 2278789 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][O:9][C:10]1[C:15]([CH3:16])=[CH:14][C:13]([C:17]2[N:21]=[C:20]([C:22]3[CH:27]=[C:26]([O:28][CH3:29])[N:25]=[C:24]([CH:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)[CH:23]=3)[O:19][N:18]=2)=[CH:12][C:11]=1[CH2:35][CH3:36])(=O)=O.Cl.C[O:39][C:40]([CH:42]1[CH2:45][NH:44][CH2:43]1)=[O:41]>>[CH:30]1([C:24]2[CH:23]=[C:22]([C:20]3[O:19][N:18]=[C:17]([C:13]4[CH:14]=[C:15]([CH3:16])[C:10]([O:9][CH2:8][CH2:7][CH2:6][N:44]5[CH2:45][CH:42]([C:40]([OH:39])=[O:41])[CH2:43]5)=[C:11]([CH2:35][CH3:36])[CH:12]=4)[N:21]=3)[CH:27]=[C:26]([O:28][CH3:29])[N:25]=2)[CH2:31][CH2:32][CH2:33][CH2:34]1

Participants

3

Reactant 2

HCID 21100040Methyl azetidine-3-carboxylate hydrochlorideHCID 86702021HCID 86702021, compound

Product 1

HCID 57524621HCID 57524621, compoundYield 19.1%

Procedure

The title compound (29 mg) is prepared as a white solid in analogy to the procedures given in Example 1 starting from 3-(4-(5-(2-cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenoxy)propyl methanesulfonate (150 mg, 0.291 mmol) and azetidine-3-carboxylic acid methyl ester hydrochloride (220 mg, 1.46 mmol); LC-MS: tR=0.96 min, [M+H]+=521.39; 1H NMR (CD3OD): δ 7.89 (d, J=1.4 Hz, 1H), 7.87 (d, J=1.4 Hz, 1H), 7.55 (d, J=1.0 Hz, 1H), 7.31 (d, J=1.1 Hz, 1H), 4.24-4.40 (m, 4H), 4.01 (s, 3H), 3.97 (t, J=5.8 Hz, 2H), 3.53-3.60 (m, 2H), 3.43-3.48 (m, 1H), 3.26-3.31 (m, 1H), 2.78 (q, J=7.5 Hz, 2H), 2.41 (s, 3H), 2.06-2.19 (m, 4H), 1.86-1.97 (m, 4H), 1.72-1.83 (m, 2H), 1.33 (t, J=7.5 Hz, 3H).

Sources & evidence

ORD record
ord-1360e7a9bfa14b538a42a6404d448f27
Source dataset
uspto-grants-2015_09
Patent number
US09133179B2

Reaction notes

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