2-Chloropyridine → HCID 56965700, compound

HRID 2422002Notes

Reaction equation

HRID 2422002 reaction equation
ClC1C=CC=CN=1.N1CC(NC(=O)OC(C)(C)C)C1.Cl[C:21]1[C:22]([N:31]2[CH2:34][CH:33]([NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])[CH2:32]2)=[N:23][CH:24]=[C:25](C(F)(F)F)[CH:26]=1>>[N:23]1[CH:24]=[CH:25][CH:26]=[CH:21][C:22]=1[N:31]1[CH2:34][CH:33]([NH:35][C:36](=[O:42])[O:37][C:38]([CH3:40])([CH3:39])[CH3:41])[CH2:32]1

Participants

4

Reactant 3

HCID 79772-ChloropyridineHCID 15194053-Aminoazetidine, 3-BOC protectedHCID 86625879HCID 86625879, compound

Product 1

HCID 56965700HCID 56965700, compound

Procedure

The title compound was prepared from 2-chloropyridine and tert-butyl azetidin-3-ylcarbamate in a similar manner as described for tert-butyl {1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]azetidin-3-yl}carbamate. 1H NMR (500 MHz CDCl3): δ 1.46 (s, 9H), 3.76-3.80 (m, 2H), 4.31-4.35 (m, 2H), 4.63 (bs, 1H), 5.10 (bs, 1H), 6.29 (d, 1H), 6.61-6.64 (m, 1H), 7.43-7.47 (m, 1H), 8.14-8.16 (m, 1H); 13C NMR (125 MHz CDCl3): δ 28.58, 41.79, 58.58, 80.22, 106.36, 113.48, 137.37, 148.42, 155.24, 160.66; Mass Spectrum: M+H+ 250.

Sources & evidence

ORD record
ord-8457ee016c9b48ce82780c6f65070282
Source dataset
uspto-grants-2011_06
Patent number
US07960380B2

Reaction notes

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