Water → 6-(2-Methoxy-ethyl)-2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-1,4,5,6,7,8-hexahydro-imidazo[4,5-d]azepine

HRID 1244370Notes

Reaction equation

HRID 1244370 reaction equation
[CH3:1][O:2][CH2:3][C:4]([N:6]1[CH2:12][CH2:11][C:10]2[N:13]=[C:14]([C:16]3[S:17][C:18]4[C:24]([N:25]5[CH2:30][CH2:29][O:28][CH2:27][CH2:26]5)=[CH:23][CH:22]=[C:21]([O:31][CH3:32])[C:19]=4[N:20]=3)[NH:15][C:9]=2[CH2:8][CH2:7]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OC(=O)C)C.O>O1CCCC1>[CH3:1][O:2][CH2:3][CH2:4][N:6]1[CH2:7][CH2:8][C:9]2[N:15]=[C:14]([C:16]3[S:17][C:18]4[C:24]([N:25]5[CH2:30][CH2:29][O:28][CH2:27][CH2:26]5)=[CH:23][CH:22]=[C:21]([O:31][CH3:32])[C:19]=4[N:20]=3)[NH:13][C:10]=2[CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 11282527HCID 11282527, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 113966256-(2-Methoxy-ethyl)-2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-1,4,5,6,7,8-hexahydro-imidazo[4,5-d]azepineYield 53.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.09 g 2-Methoxy-1-[2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-4,5,7,8-tetrahydro-1H-imidazo[4,5-d]azepin-6-yl]-ethanone in 5 ml tetrahydrofurane were reacted with 0.2 ml lithiumaluminium hydride solution (1 M in tetrahydrofurane) over night at room temperature. 5 ml ethylacetate was added followed by 5 ml water at 0–5° C. Extraction with ethylacetate and chromatography on silicagel with dichloromethane/methanol 96:4 yielded 0.047 g (53%) 6-(2-methoxy-ethyl)-2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-1,4,5,6,7,8-hexahydro-imidazo[4,5-d]azepine as yellow solid; MS (ISP): m/e=444 (M+H+).

Workup

  1. extractionExtraction with ethylacetate and chromatography on silicagel with dichloromethane/methanol 96:4

Sources & evidence

ORD record
ord-379a555855894ff697e6ed6783d5a362
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

Loading…