Acetic Anhydride → HCID 22961877, compound

HRID 365928Notes

Reaction equation

[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([O:10][CH2:11][C@@H:12]2[CH2:15][CH2:14][N:13]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:6]=[N:7][C:8]=1[Cl:9].[C:23](OC(=O)C)(=[O:25])[CH3:24]>>[C:23]([NH:1][CH2:2][C:3]1[CH:4]=[C:5]([O:10][CH2:11][C@@H:12]2[CH2:15][CH2:14][N:13]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:6]=[N:7][C:8]=1[Cl:9])(=[O:25])[CH3:24]

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 22872662HCID 22872662, compound

Product 1

HCID 22961877HCID 22961877, compoundYield 76%

Procedure

5-Aminomethyl-3-(1-BOC-2-(S)-azetidinylmethoxy)-6-chloropyridine (0.19 g, 0.60 mmol) from Example 92b was treated with acetic anhydride and further processed according to the procedure of Example 205c to afford the title compounds in 76% yield. 1H NMR (CDCl3, 300 MHz) δ 1.40 (s, 9H), 2.04 (s, 3H), 2.10-2.19 (m, 2H), 3.85 (t, J=7.5 Hz, 2H), 4.10 (dd, J=3.0, 10.5 Hz, 1H), 4.31 (m, 1H), 4.42-4.57 (m, 3H), 7.38 (d, J=3.0 Hz, 1H), 8.04 (d, J=3.0 Hz, 1H); MS (CI/NH3) m/z 370 (M+H)+.

Sources & evidence

ORD record: ord-34dff2c745904668afbb3ef86dbc6f53
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06127386

Reaction notes

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