Diisopropylethylamine → N-[1-(2,3-dichlorobenzyl)pyrrolidin-3-(RS)-ylmethyl]-2-[5-(4-methoxyphenyl)pyrimidin-2-ylamino]acetamide HCl salt

HRID 1276371Notes

Reaction equation

HRID 1276371 reaction equation
Cl.C[N:3](C)[CH2:4][CH2:5][CH2:6][N:7]=[C:8]=[N:9][CH2:10][CH3:11].[NH2:13][CH2:14][CH:15]1[CH2:19][CH2:18][N:17]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:22]=2[Cl:28])[CH2:16]1.[CH3:29][O:30][C:31]1[CH:32]=[C:33](C2C=NC(NCC(O)=O)=NC=2)[CH:34]=[CH:35][CH:36]=1.O.[OH:49]N1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[ClH:27].[Cl:28][C:22]1[C:23]([Cl:27])=[CH:24][CH:25]=[CH:26][C:21]=1[CH2:20][N:17]1[CH2:18][CH2:19][CH:15]([CH2:14][NH:13][C:11](=[O:49])[CH2:10][NH:9][C:8]2[N:3]=[CH:4][C:5]([C:34]3[CH:33]=[CH:32][C:31]([O:30][CH3:29])=[CH:36][CH:35]=3)=[CH:6][N:7]=2)[CH2:16]1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 114368453-(RS)-aminomethyl-1-(2,3-dichlorobenzyl)-pyrrolidineHCID 221153602-[5-(3-Methoxyphenyl)pyrimidin-2-ylamino]acetic acid

Product 1

HCID 9871880N-[1-(2,3-dichlorobenzyl)pyrrolidin-3-(RS)-ylmethyl]-2-[5-(4-methoxyphenyl)pyrimidin-2-ylamino]acetamide HCl saltYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Solid 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (14 mg, 0.08 mmol, 1.5 equiv.) was added to a solution of 3-(RS)-aminomethyl-1-(2,3-dichlorobenzyl)-pyrrolidine (13 mg, 0.05 mmol), 2-[5-(3-methoxyphenyl)pyrimidin-2-ylamino]acetic acid (16 mg, 0.06 mmol, 1.2 equiv.), 1-hydroxybenzotriazole hydrate (10 mg, 0.08 mmol, 1.5 equiv.) and diisopropylethylamine (22 mL, 0.13 mmol, 2.5 equiv.) in dimethyl formamide (0.5 mL). The reaction mixture was shaken at room temperature overnight. The reaction mixture was quenched with methanol (0.3 mL), then purified directly by reverse phase preparative HPLC to give N-[1-(2,3-dichlorobenzyl)pyrrolidin-3-(RS)-ylmethyl]-2-[5-(4-methoxyphenyl)pyrimidin-2-ylamino]acetamide HCl salt (11 mg).

Workup

  1. customThe reaction mixture was quenched with methanol (0.3 mL)
  2. custompurified directly by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-740fe55dfa3c4979a8078e1ec715cece
Source dataset
uspto-grants-2000_12
Patent number
US06166015

Reaction notes

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