3-Hydroxybenzoic Acid → HCID 66746799, compound

HRID 1467027Notes

Reaction equation

HRID 1467027 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[C:3]=1[C:4]#[N:5].[OH:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22](O)=[O:23]>>[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][CH:12]2[CH2:17][CH2:16][N:15]([C:22](=[O:23])[C:21]3[CH:25]=[CH:26][CH:27]=[C:19]([OH:18])[CH:20]=3)[CH2:14][CH2:13]2)[C:3]=1[C:4]#[N:5]

Participants

3

Reactant 2

HCID 74203-Hydroxybenzoic AcidHCID 66746694HCID 66746694, compound

Product 1

HCID 66746799HCID 66746799, compound

Procedure

Prepared as in Example 24a from 2-amino-6-(piperidin-4-ylmethoxy)benzonitrile (Example 34c) and 3-hydroxybenzoic acid as an orange glass (66%). 1H NMR (400 MHz, DMSO-d6) δ 1.29 (m, 2H), 1.66-1.92 (m, 2H), 2.06 (m, 1H), 2.80 (brs, 1H), 3.05 (brs, 1H), 3.62 (brs, 1H), 3.91 (d, J=8.0 Hz, 2H), 4.49 (brs, 1H), 5.99 (s, 2H), 6.22 (d, J=8.0 Hz, 1H), 6.34 (d, J=8.0 Hz, 1H), 6.72-6.83 (m, 3H), 7.15-7.24 (m, 2H), 9.65 (s, 1H). MS 352 (MH+).

Sources & evidence

ORD record
ord-c674f33997144bbdbc08dff838a8f44f
Source dataset
uspto-grants-2015_04
Patent number
US09000054B2

Reaction notes

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