4-Bis(2-pyridylmethyl)aminomethyl-2-(5-methoxy-2-methoxymethoxyphenyl)benzoxazole → 4-Bis(2-pyridylmethyl)aminomethyl-2-(2,5-dimethoxyphenyl)benzoxazole

HRID 2214002Notes

Reaction equation

HRID 2214002 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]([CH2:16][C:17]1[C:22]2[N:23]=[C:24]([C:26]3[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:27]=3[O:34][CH2:35]OC)[O:25][C:21]=2[CH:20]=[CH:19][CH:18]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.BrCC1C2N=C(C3C=C(OC)C=CC=3OC)OC=2C=CC=1>>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]([CH2:16][C:17]1[C:22]2[N:23]=[C:24]([C:26]3[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:27]=3[O:34][CH3:35])[O:25][C:21]=2[CH:20]=[CH:19][CH:18]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

3

Reactant 2

HCID 219593114-Bis(2-pyridylmethyl)aminomethyl-2-(5-methoxy-2-methoxymethoxyphenyl)benzoxazoleHCID 219593194-Bromomethyl-2-(2,5-dimethoxyphenyl)benzoxazole

Product 1

HCID 219593314-Bis(2-pyridylmethyl)aminomethyl-2-(2,5-dimethoxyphenyl)benzoxazole

Procedure

4-bis(2-pyridylmethyl)aminomethyl-2-(2,5-dimethoxy phenyl)benzoxazole (F22) was prepared in a similar manner for the preparation of 4-bis(2-pyridylmethyl)aminomethyl-2-(5-methoxy-2-methoxymethoxyphenyl)benzoxazole (F18) using 4-bromomethyl-2-(2,5-dimethoxyphenyl)benzoxazole (F14) (522 mg, 1.5 mmol) instead of 4-bromomethyl-2-(5-methoxy-2-methoxymethoxyphenyl)benzoxazole (F12) in 91% (640 mg); 1H-NMR (400 MHz, CDCl3) δ3.88 (s, 4H), 3.95 (s, 6H), 4.23 (s, 2H), 7.01–7.07 (m, 2H), 7.13 (dd, 2H, J=8.0, 5.0 Hz), 7.34 (t, 1H, J=7.5 Hz), 7.49 (d, 1H, J=7.5 Hz), 7.57 (d, 1H, J=7.5 Hz), 7.64–7.68 (m, 3H), 7.80 (d, 2H, J=8.0 Hz), 8.52 (d, 2H, J=5.0 Hz).

Sources & evidence

ORD record
ord-5ff5f1e22ebc49879fed9cc619a58f6d
Source dataset
uspto-grants-2006_09
Patent number
US07105680B1

Reaction notes

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