Acetyl chloride → HCID 69015093, compound

HRID 1455072Notes

Reaction equation

HRID 1455072 reaction equation
C(NC1C=CC([O:11][C:12]2[CH:13]=[C:14]([CH:18]3[CH2:27][CH2:26][C:25]4[C:20](=[CH:21][CH:22]=[C:23]([O:28][C:29]5[N:34]=[CH:33][C:32]([NH:35][C:36](=[O:38])[CH3:37])=[CH:31][CH:30]=5)[CH:24]=4)[O:19]3)[CH:15]=[CH:16][CH:17]=2)=NC=1)(=O)C.NC1C=CC(OC2C=C3C(=CC=2)OC(C2C=C(O)C=CC=2)CC3)=NC=1.C(Cl)(C)=O>>[OH:11][C:12]1[CH:13]=[C:14]([CH:18]2[CH2:27][CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[C:23]([O:28][C:29]4[N:34]=[CH:33][C:32]([NH:35][C:36](=[O:38])[CH3:37])=[CH:31][CH:30]=4)[CH:24]=3)[O:19]2)[CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 69016404HCID 69016404, compoundHCID 69016749HCID 69016749, compound

Product 1

HCID 69015093HCID 69015093, compound

Procedure

N-{6-[2-(3-Hydroxyphenyl)chroman-6-yloxy]pyridin-3-yl}acetamide was prepared as described for N-(6-{2-[3-(5-acetylaminopyridin-2-yloxy)-phenyl]-chroman-6-yloxy}pyridin-3-yl)acetamide in Example 57 starting from 3-[6-(5-aminopyridin-2-yloxy)chroman-2-yl]phenol using 1.2 eq. AcCl. 1H NMR (400 MHz, d6-DMSO) δ: 10.03 (s, 1H), 9.42 (s, 1H), 8.27 (d, 1H, J 2.6 Hz), 8.01 (dd, 1H, J 8.8, 2.6 Hz), 7.18 (t, 1H, J 8.0 Hz), 6.93 (d, 1H, J 8.8 Hz), 6.84-6.85 (m, 5H), 6.72 (d, 1H, J 8.9 Hz), 5.03 (d, 1H, J 8.2 Hz), 2.94 (m, 1H), 2.70 (m, 1H), 2.14 (m, 1H), 2.04 (s, 3H), 1.94 (m, 1H).

Sources & evidence

ORD record
ord-82f42f32a8994de1a6a627905b74d489
Source dataset
uspto-grants-2009_01
Patent number
US07482340B2

Reaction notes

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