4-Carboxy-1,2,3-triazole → HCID 178523372, compound

HRID 870611Notes

Reaction equation

HRID 870611 reaction equation
Cl.CN(C)CCCN=C=NCC.[N:13]1[NH:14][N:15]=[C:16]([C:18]([OH:20])=O)[CH:17]=1.[NH2:21][CH2:22][CH2:23][C:24]([N:26]1[CH2:45][CH2:44][C:29]2[N:30]=[C:31]([NH:34][CH:35]3[CH2:43][C:42]4[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=4)[CH2:36]3)[N:32]=[CH:33][C:28]=2[CH2:27]1)=[O:25]>CN(C)C1C=CN=CC=1.ClCCl>[CH2:36]1[C:37]2[C:42](=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:43][CH:35]1[NH:34][C:31]1[N:32]=[CH:33][C:28]2[CH2:27][N:26]([C:24](=[O:25])[CH2:23][CH2:22][NH:21][C:18]([C:16]3[N:15]=[N:14][NH:13][CH:17]=3)=[O:20])[CH2:45][CH2:44][C:29]=2[N:30]=1

Participants

6

Reactant 3

HCID 1401204-Carboxy-1,2,3-triazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86726575HCID 86726575, compound

Product 1

HCID 178523372HCID 178523372, compoundYield 63%

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 2H-triazole-4-carboxylic acid (0.048 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 at ambient temperature for 16 hours. Load the mixture directly onto a silica gel column and purify by column chromatography (0 to 10% methanol in ethyl acetate) to afford N-{3-[2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]-3-oxopropyl}-1H-1,2,3-triazole-4-carboxamide (0.105 g; 63%) as a white solid: MS (m/z): 433(M+1).

Workup

  1. customthe reaction at ambient temperature for 16 hours
  2. customLoad the mixture directly onto a silica gel column and purify by column chromatography (0 to 10% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-f8d410e52aaa4d28a03722f2e685e9c9
Source dataset
uspto-grants-2015_03
Patent number
US08969555B2

Reaction notes

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