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

HRID 2214004Notes

Reaction equation

HRID 2214004 reaction equation
COC1C=CC(O)=C(C2OC3C=CC=C(CNCC4C=CC=CN=4)C=3N=2)C=1.[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH2:34][N:35]([CH2:43][C:44]1[C:49]2[N:50]=[C:51]([C:53]3[CH:58]=[C:57]([O:59][CH3:60])[CH:56]=[CH:55][C:54]=3[O:61]COC)[O:52][C:48]=2[CH:47]=[CH:46][CH:45]=1)[CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=1>>[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH2:34][N:35]([CH2:43][C:44]1[C:49]2[N:50]=[C:51]([C:53]3[CH:58]=[C:57]([O:59][CH3:60])[CH:56]=[CH:55][C:54]=3[OH:61])[O:52][C:48]=2[CH:47]=[CH:46][CH:45]=1)[CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=1

Participants

3

Reactant 2

HCID 219593114-Bis(2-pyridylmethyl)aminomethyl-2-(5-methoxy-2-methoxymethoxyphenyl)benzoxazoleHCID 1357441682-(5-Methoxy-2-hydroxyphenyl)-4-(2-pyridylmethyl)aminomethylbenzoxazole

Product 1

HCID 1357441704-Bis(2-pyridylmethyl)aminomethyl-2-(2-hydroxy-5-methoxyphenyl)benzoxazole

Procedure

4-bis(2-pyridylmethyl)aminomethyl-2-(2-hydroxy-5-methoxyphenyl)benzoxazole (F25) was prepared in a similar manner for the preparation of 2-(5-methoxy-2-hydroxyphenyl)-4-(2-pyridylmethyl)aminomethylbenzoxazole (F23) using 4-bis(2-pyridylmethyl)aminomethyl-2-(5-methoxy-2-methoxymethoxyphenyl)benzoxazole (F17) (136 mg, 0.275 mmol) instead of 2-(5-methoxy-2-methoxymethoxyphenyl)-4-(2-pyridylmethyl)aminomethylbenzoxazole (F16) in 98% (122 mg); 1H-NMR (500 MHz, CDCl3) δ3.87 (s, 3H), 3.89 (s, 4H), 4.12 (s, 2H), 7.06 (br s, 2H), 7.14 (dd, 1H, J=7.5, 4.0 Hz), 7.35 (t, 1H, J=8.0 Hz), 7.49–7.53 (m, 3H), 7.64–7.70 (m, 4H), 8.52 (d, 2H, J=4.0 Hz), 11.06 (s, 1H).

Sources & evidence

ORD record
ord-5f6ae0fed0d54dbaa2d1ad56af002627
Source dataset
uspto-grants-2006_09
Patent number
US07105680B1

Reaction notes

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