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

HRID 2214001Notes

Reaction equation

HRID 2214001 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](OC)[CH:29]=[CH:28][C:27]=3OCOC)[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[C:52]([O:55][CH2:56][O:57]C)=CC=3)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]=[CH:30][C:29]([O:57][CH2:56][O:55][CH3:52])=[CH:28][CH:27]=3)[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 219593284-Bromomethyl-2-(4-methoxymethoxyphenyl)benzoxazole

Product 1

HCID 219593124-Bis(2-pyridylmethyl)aminomethyl-2-(4-methoxymethoxyphenyl)benzoxazole

Procedure

4-bis(2-pyridylmethyl)aminomethyl-2-(4-methoxymethoxyphenyl)benzoxazole (F21) 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-(4-methoxymethoxyphenyl)benzoxazole (F15) (552 mg, 1.5 mmol) instead of 4-bromomethyl-2-(5-methoxy-2-methoxymethoxyphenyl)benzoxazole (F12) in 98% (704 mg); 1H-NMR (400 MHz, CDCl3) δ3.52 (s, 3H), 3.93 (s, 4H), 4.19 (s, 2H), 5.26 (s, 2H), 7.11–7.18 (m, 4H), 7.29 (t, 1H, J=8.0 Hz), 7.44 (d, 1H, J=8.0 Hz), 7.51 (d, 1H, J=8.0 Hz), 7.66 (d, 2H, J=7.6 Hz), 7.78 (d, 2H, J=7.6 Hz), 8.19 (d, 2H, J=9.2 Hz), 8.55 (d, 2H, J=5.0 Hz).

Sources & evidence

ORD record
ord-ac645990e9074eeea3ae7ca4605ab71b
Source dataset
uspto-grants-2006_09
Patent number
US07105680B1

Reaction notes

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