2-(4,5-Dimethoxy-2-methoxymethoxyphenyl)-4-(2-pyridylmethyl)aminomethylbenzoxazole → 2-(4,5-Dimethoxy-2-hydroxyphenyl)-4-(2-pyridylmethyl) aminomethylbenzoxazole

HRID 2214005Notes

Reaction equation

HRID 2214005 reaction equation
COC1C=CC(O)=C(C2OC3C=CC=C(CNCC4C=CC=CN=4)C=3N=2)C=1.[CH3:28][O:29][C:30]1[C:35]([O:36][CH3:37])=[CH:34][C:33]([C:38]2[O:39][C:40]3[CH:46]=[CH:45][CH:44]=[C:43]([CH2:47][NH:48][CH2:49][C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][N:51]=4)[C:41]=3[N:42]=2)=[C:32]([O:56]COC)[CH:31]=1>>[CH3:28][O:29][C:30]1[C:35]([O:36][CH3:37])=[CH:34][C:33]([C:38]2[O:39][C:40]3[CH:46]=[CH:45][CH:44]=[C:43]([CH2:47][NH:48][CH2:49][C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][N:51]=4)[C:41]=3[N:42]=2)=[C:32]([OH:56])[CH:31]=1

Participants

3

Reactant 2

HCID 219593292-(4,5-Dimethoxy-2-methoxymethoxyphenyl)-4-(2-pyridylmethyl)aminomethylbenzoxazoleHCID 1357441682-(5-Methoxy-2-hydroxyphenyl)-4-(2-pyridylmethyl)aminomethylbenzoxazole

Product 1

HCID 1354286942-(4,5-Dimethoxy-2-hydroxyphenyl)-4-(2-pyridylmethyl) aminomethylbenzoxazole

Procedure

2-(4,5-dimethoxy-2-hydroxyphenyl)-4-(2-pyridylmethyl)aminomethyl-benzoxazole (F26) was prepared in a similar manner for the preparation of 2-(5-methoxy-2-hydroxyphenyl)-4-(2-pyridylmethyl)aminomethylbenzoxazole (F23) using 2-(4,5-dimethoxy-2-methoxymethoxyphenyl)-4-(2-pyridylmethyl)aminomethylbenzoxazole (F17) (100 mg, 0.23 mmol) instead of 2-(5-methoxy-2-methoxymethoxyphenyl)-4-(2-pyridylmethyl)aminomethylbenzoxazole (F16) in 92% (83 mg); 1H-NMR (500 MHz, CDCl3) δ3.95 (s, 3H), 3.96 (s, 3H), 4.01 (s, 2H), 4.21 (s, 2H), 6.66 (s, 1H), 7.17 (dd, 1H, J=7.5, 5.0 Hz), 7.31 (t, 1H, J=8.0 Hz), 7.37–7.40 (m, 2H), 7.41 (s, 1H), 7.48 (d, 1H, J=8.0 Hz),7.67 (t, 1H, J=7.5 Hz), 8.66 (d, 2H, J=5.0 Hz), 11.27 (s, 1H).

Sources & evidence

ORD record
ord-fb924c59d067462887bec775412c8d8a
Source dataset
uspto-grants-2006_09
Patent number
US07105680B1

Reaction notes

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