10-bromo-5-hydroxy-2-(3-pyridylmethyl)-3H-pyrido[3,2,1-kl]phenothiazin-3-one → 5-(5-acetoxymethyl-3-pyridylmethyloxy)-10-bromo-2-(3-pyridylmethyl)-3H-pyrido[3,2,1-kl]phenothiazin-3-one

HRID 1016310Notes

Reaction equation

HRID 1016310 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6]4=[C:7]([C:17](=[O:27])[C:18]([CH2:20][C:21]5[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=5)=[CH:19][N:5]4[C:4]=2[CH:3]=1)[CH:8]=[C:9]([OH:16])[CH:10]=3.Cl[CH2:29][C:30]1[CH:31]=[N:32][CH:33]=[C:34]([CH2:36][O:37][C:38](=[O:40])[CH3:39])[CH:35]=1>>[C:38]([O:37][CH2:36][C:34]1[CH:35]=[C:30]([CH2:29][O:16][C:9]2[CH:10]=[C:11]3[C:6]4=[C:7]([C:17](=[O:27])[C:18]([CH2:20][C:21]5[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=5)=[CH:19][N:5]4[C:4]4[CH:3]=[C:2]([Br:1])[CH:15]=[CH:14][C:13]=4[S:12]3)[CH:8]=2)[CH:31]=[N:32][CH:33]=1)(=[O:40])[CH3:39]

Participants

3

Reactant 2

HCID 1202110510-bromo-5-hydroxy-2-(3-pyridylmethyl)-3H-pyrido[3,2,1-kl]phenothiazin-3-oneHCID 184066143-Chloromethyl-5-acetoxymethylpyridine

Product 1

HCID 184065815-(5-acetoxymethyl-3-pyridylmethyloxy)-10-bromo-2-(3-pyridylmethyl)-3H-pyrido[3,2,1-kl]phenothiazin-3-oneYield 77%

Procedure

According to Example 34, the compound (250 mg) produced in Example 37 was reacted with 3-chloromethyl-5-acetoxymethylpyridine (175 mg) to obtain the title compound (260 mg; 77%).

Sources & evidence

ORD record
ord-c0f08de0b8fb4f81acddbc2800eae1b7
Source dataset
uspto-grants-2002_11
Patent number
US06476021B1

Reaction notes

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