Sodium hydride → HCID 57448365, compound

HRID 1807470Notes

Reaction equation

HRID 1807470 reaction equation
[S:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]1[O:10][C:11]1[CH:23]=[CH:22][C:14]([O:15][CH2:16][CH2:17][NH:18][CH:19]2[CH2:21][CH2:20]2)=[CH:13][CH:12]=1.[H-].[Na+]>>[CH3:2][O:10][CH2:11][CH2:12][CH2:13][N:18]([CH2:17][CH2:16][O:15][C:14]1[CH:22]=[CH:23][C:11]([O:10][C:2]2[S:1][C:9]3[C:4]([N:3]=2)=[N:5][CH:6]=[CH:7][CH:8]=3)=[CH:12][CH:13]=1)[CH:19]1[CH2:21][CH2:20]1

Participants

3

Reactant 2

HCID 24758Sodium hydrideHCID 57448293HCID 57448293, compound

Product 1

HCID 57448365HCID 57448365, compound

Procedure

The title compound was prepared from N-{2-[4-([1,3]thiazolo[4,5-b]pyridin-2-yloxy)phenoxy]ethyl}cyclopropanamine using methods analogous to those described for Example 271, using more sodium hydride (2.5 equiv.) and more of the appropriate amine (2 equiv.). 1H NMR (500 MHz, CDCl3): 8.58 (dd, J=4.8, 1.6, 1H), 8.01 (dd, J=7.9, 1.7, 1H), 7.35-7.30 (m, 2H), 7.21 (dd, J=7.9, 4.8, 1H), 6.98-6.93 (m, 2H), 4.13 (t, J=6.2, 2H), 3.43 (t, J=6.4, 2H), 3.35 (s, 3H), 3.05 (t, J=6.2, 2H), 2.82-2.77 (m, 2H), 1.92-1.80 (m, 3H), 0.55-0.42 (m, 4H). MS (ESI): mass calcd. for C21H25N3O3S, 399.16; m/z found, 400.1 [M+H]+.

Sources & evidence

ORD record
ord-ae793070f44d49f8a6f37ef1d7bc6e2a
Source dataset
uspto-grants-2013_01
Patent number
US08357684B2

Reaction notes

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