1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 178520363, compound

HRID 870610Notes

Reaction equation

HRID 870610 reaction equation
Cl.CN(C)CCCN=C=NCC.[N:13]1[NH:14][N:15]=[C:16]([CH2:18][C:19]([NH2:21])=[O:20])[CH:17]=1.N[CH2:23][CH2:24][C:25]([N:27]1[CH2:46][CH2:45][C:30]2[N:31]=[C:32]([NH:35][CH:36]3[CH2:44][C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[CH2:37]3)[N:33]=[CH:34][C:29]=2[CH2:28]1)=[O:26]>CN(C)C1C=CN=CC=1.ClCCl>[CH2:37]1[C:38]2[C:43](=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:44][CH:36]1[NH:35][C:32]1[N:33]=[CH:34][C:29]2[CH2:28][N:27]([C:25](=[O:26])[CH2:24][CH2:23][NH:21][C:19](=[O:20])[CH2:18][C:16]3[NH:15][N:14]=[N:13][CH:17]=3)[CH2:46][CH2:45][C:30]=2[N:31]=1

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 20389367HCID 20389367, compoundHCID 86726575HCID 86726575, compound

Product 1

HCID 178520363HCID 178520363, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Add 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.111 g; 1.5 equiv; 0.58 mmoles) to a solution of 2-(2H-triazol-4-yl)acetamide (0.056 g; 1.1 equiv; 0.42 mmoles), 3-amino-1-[2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]propan-1-one (0.13 g; 1.0 equiv; 0.39 mmoles), and N,N-dimethyl-4-pyridinamine, (0.0094 g; 0.2 equiv; 0.077 mmoles) in dichloromethane (1.28 mL). Stir the reaction mixture for 16 hours at ambient temperature. Load the solution directly onto a silica gel column and purify by column chromatography (0 to 10% methanol in dichloromethane) to give N-{3-[2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]-3-oxopropyl}-2-(1H-1,2,3-triazol-5-yl)acetamide (0.098 g; 57%) as a white solid: MS (m/z): 447(M+1).

Workup

  1. customLoad the solution directly onto a silica gel column and purify by column chromatography (0 to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-5c29ab570d6948f68230e56bbf6a3341
Source dataset
uspto-grants-2015_03
Patent number
US08969555B2

Reaction notes

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