Methyl 2-(bromomethyl)benzoate → 7-Chloro-6-(2-methoxycarbonylbenzylthio)-2,3,4,5-tetrahydro-1H-benzo[d]azepine Hydrochloride
Reaction equation
C(OC(N1CCC2C(SC(=O)N(C)C)=C([Cl:19])C=CC=2CC1)=O)(C)(C)C.C(OC([N:33]1[CH2:39][CH2:38][C:37]2[C:40]([S:46][C:47](=O)N(C)C)=[C:41]([Cl:45])[CH:42]=[C:43](Cl)[C:36]=2[CH2:35][CH2:34]1)=O)(C)(C)C.BrC[C:54]1[CH:63]=[CH:62][CH:61]=[CH:60][C:55]=1[C:56]([O:58][CH3:59])=[O:57]>>[ClH:19].[Cl:45][C:41]1[CH:42]=[CH:43][C:36]2[CH2:35][CH2:34][NH:33][CH2:39][CH2:38][C:37]=2[C:40]=1[S:46][CH2:47][C:54]1[CH:63]=[CH:62][CH:61]=[CH:60][C:55]=1[C:56]([O:58][CH3:59])=[O:57]Participants
4
Reactant 3
Product 1
Procedure
Use a method similar to the Example 347, using the 4:1 mixture of 3-tert-butoxycarbonyl-7-chloro-6-dimethylcarbamoylthio-2,3,4,5-tetrahydro-1H-benzo[d]azepine and 3-tert-butoxycarbonyl-7,9-dichloro-6-dimethylcarbamoylthio-2,3,4,5-tetrahydro-benzo[d]azepine with methyl 2-(bromomethyl)benzoate. Use a method similar to the General Procedure 1-4 and purify by preparative reverse phase HPLC (Column: Xterra Prep RP18 19×250 mm; solvent A: 10 mM aqueous ammonium carbonate, solvent B: acetonitrile; 30-100% B over 20 minutes; flow rate 25 mL/min). Use a method similar to the General Procedure 2-2, to give the title compound as a white solid. MS (ES+) m/z: 362 (M+H)+.
Workup
- custompurify by preparative reverse phase HPLC (Column: Xterra Prep RP18 19×250 mm; solvent A: 10 mM aqueous ammonium carbonate, solvent B: acetonitrile; 30-100% B over 20 minutes; flow rate 25 mL/min)
Sources & evidence
- ORD record
- ord-8a3852b5e4ff42deb6fa916964bb3526
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08022062B2
Reaction notes
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