5-Bromopentanenitrile → HCID 66707308, compound

HRID 911541Notes

Reaction equation

HRID 911541 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([S:20][C:21](=O)N(C)C)=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C.BrC[CH2:28][CH2:29][CH2:30][C:31]#[N:32]>>[ClH:19].[Cl:19][C:16]1[CH:17]=[CH:18][C:11]2[CH2:10][CH2:9][NH:8][CH2:14][CH2:13][C:12]=2[C:15]=1[S:20][CH2:21][CH2:28][CH2:29][CH2:30][C:31]#[N:32]

Participants

3

Reactant 2

HCID 794355-BromopentanenitrileHCID 576559793-tert-butoxycarbonyl-7-chloro-6-dimethylaminocarbonylthio-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 66707308HCID 66707308, compound

Procedure

Use a method similar to the Example 387 to react 3-tert-butoxycarbonyl-7-chloro-6-dimethylcarbamoylthio-2,3,4,5-tetrahydro-1H-benzo[d]azepine with 5-bromovaleronitrile. 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 an off-white solid. MS (APCI+) m/z: 295 (M+H)+.

Workup

  1. 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-51d969267cd14e67a6451154d80273a8
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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