HCID 21959314, compound → 2-(4,5-Dimethoxy-2-hydroxyphenyl)-4-(2-pyridylmethyl) aminomethylbenzoxazole

HRID 855926Notes

Reaction equation

HRID 855926 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([O:27]COC)=[C:7]([C:9]2[O:10][C:11]3[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][NH:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)[C:12]=3[N:13]=2)[CH:8]=1.BrCC1C2N=[C:40](C3C=C(OC)C(OC)=CC=3OCOC)[O:41]C=2C=CC=1>>[CH3:40][O:41][C:4]1[C:3]([O:2][CH3:1])=[CH:8][C:7]([C:9]2[O:10][C:11]3[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][NH:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)[C:12]=3[N:13]=2)=[C:6]([OH:27])[CH:5]=1

Participants

3

Reactant 2

HCID 21959314HCID 21959314, compoundHCID 219593354-Bromomethyl-2-(4,5-dimethoxy-2-methoxymethoxyphenyl)benzoxazole

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 (F19) was prepared in a similar manner for the preparation of 2-(5-methoxy-2-methoxymethoxyphenyl)-4-(2-pyridylmethyl)aminomethylbenzoxazole (F16) using 4-bromomethyl-2-(4,5-dimethoxy-2-methoxymethoxyphenyl)benzoxazole (F13) (612 mg, 1.59 mmol) instead of 4-bromomethyl-2-(5-methoxy-2-methoxymethoxyphenyl)benzoxazole (F12) in 17% (112 mg); 1H-NMR (500 MHz, CDCl3) δ3.56 (s, 3H), 3.95 (s, 3H), 3.97 (s, 3H), 4.02 (s, 2H), 4.30 (s, 2H), 5.27 (s, 2H), 6.85 (s, 1H), 7.15 (dd, 1H, J=7.5, 5.0 Hz), 7.28 (t, 1H, J=7.5 Hz), 7.33 (d, 1H, J=7.5 Hz), 7.42 (d, 1H, J=7.5 Hz), 7.47 (d, 1H, J=7.5 Hz), 7.64 (m, 2H), 8.55 (d, 1H, J=5.0 Hz).

Sources & evidence

ORD record
ord-acd3657e39ab41879c5e403b6fb1046a
Source dataset
uspto-grants-2007_08
Patent number
US07262301B1

Reaction notes

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