Diisopropylethylamine → HCID 86716013, compound

HRID 514899Notes

Reaction equation

HRID 514899 reaction equation
[N:1]1([CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[CH2:8][NH2:9])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:16][C:17]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][C:18]=1[C:19](O)=[O:20].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:16][C:17]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][C:18]=1[C:19]([NH:9][CH2:8][CH:7]([N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)=[O:20]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2404302-Chloro-5-methylbenzoic AcidHCID 2724699PyBOPHCID 167675312-(Morpholin-4-yl)-2-(pyridin-2-yl)ethan-1-amine

Product 1

HCID 86716013HCID 86716013, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (2-morpholin-4-yl-2-pyridin-2-ylethyl)amine (62.2 mg, 0.3 mmol), 2-chloro-5-methylbenzoic acid (54 mg, 0.315 mmol), PyBOP (187 mg, 0.36 mmol) and DIPEA (78 mg, 0.60 mmol) in DCM (1.5 mL) was stirred at room temperature overnight. The mixture was purified by preparative HPLC to yield the title compound (100 mg, yield: 90%). LCMS (Mt): m/z=360.0, tR (minutes, Method A)=0.89

Workup

  1. customThe mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-25e3f1d0cff14bfc8cbb34c1701e4a85
Source dataset
uspto-grants-2015_08
Patent number
US09108938B2

Reaction notes

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