Tert-Butylamine → HCID 67323405, compound

HRID 1846686Notes

Reaction equation

HRID 1846686 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[C:5]([NH:7][C:8]1[C:9]([N:18]2[CH2:23][CH2:22][CH:21]([CH2:24][C:25]([OH:27])=O)[CH2:20][CH2:19]2)=[N:10][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:12][CH:13]=1)=[O:6].[C:31]([NH2:35])([CH3:34])([CH3:33])[CH3:32].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O.O>[C:31]([NH:35][C:25]([CH2:24][CH:21]1[CH2:22][CH2:23][N:18]([C:9]2[C:8]([NH:7][C:5](=[O:6])[C:4]3[CH:28]=[CH:29][CH:30]=[C:2]([Cl:1])[CH:3]=3)=[CH:13][CH:12]=[C:11]([S:14]([CH3:17])(=[O:16])=[O:15])[N:10]=2)[CH2:19][CH2:20]1)=[O:27])([CH3:34])([CH3:33])[CH3:32]

Participants

7

Reactant 4

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68304202HCID 68304202, compound

Product 1

HCID 67323405HCID 67323405, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.023 g (0.226 mmol) of [3′-(3-chloro-benzoylamino)-6′-methanesulfonyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl]-acetic acid, 0.011 g (0.15 mmol) of tert-butyl amine, 0.021 g (0.066 mmol) of O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate, and 0.021 mL (0.15 mmol) of triethylamine in N,N-dimethylformamide (2 mL) is stirred at room temperature for 2 hours. The mixture is diluted with water and purified using preparative reverse phase HPLC to give 0.016 g (62%) of the title compound (286) as colorless foam. [M+H]+=507.2.

Workup

  1. custompurified

Sources & evidence

ORD record
ord-b12493dd1fdc4ae58f7b558758cce749
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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