N-((1,1-dimethylethoxy)carbonyl)-beta-alanine → HCID 86726577, compound

HRID 870612Notes

Reaction equation

HRID 870612 reaction equation
Cl.CN(C)CCCN=C=NCC.[C:13]([O:17][C:18]([NH:20][CH2:21][CH2:22][C:23]([OH:25])=O)=[O:19])([CH3:16])([CH3:15])[CH3:14].[CH2:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:28][CH:27]1[NH:35][C:36]1[N:37]=[CH:38][C:39]2[CH2:45][NH:44][CH2:43][CH2:42][C:40]=2[N:41]=1>CN(C)C1C=CN=CC=1.ClCCl>[CH2:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:28][CH:27]1[NH:35][C:36]1[N:37]=[CH:38][C:39]2[CH2:45][N:44]([C:23](=[O:25])[CH2:22][CH2:21][NH:20][C:18](=[O:19])[O:17][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:43][CH2:42][C:40]=2[N:41]=1

Participants

6

Reactant 3

HCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86726522N-(indan-2-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine

Product 1

HCID 86726577HCID 86726577, compoundYield 83.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Add 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.69 g; 1.5 equiv; 14.06 mmoles) to a flask containing 3-(tert-butoxycarbonylamino)propanoic acid (1.8 g; 1.0 equiv; 9.37 mmoles), N-indan-2-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine (2.50 g; 1.0 equiv; 9.37 mmoles) and N,N-dimethyl-4-pyridinamine, (0.229 g; 0.2 equiv; 1.87 mmoles) in dichloromethane (30 mL). Stir the mixture for 2 hours, then load the solution directly onto a silica gel column and purify by column chromatography (30 to 100% ethyl acetate in dichloromethane) to give tert-butyl {3-[2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]-3-oxopropyl}carbamate (3.42 g; 83%) as a colorless foam: MS (m/z): 438(M+1).

Workup

  1. custompurify by column chromatography (30 to 100% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-04674558fb404e269e003f07ddec21b9
Source dataset
uspto-grants-2015_03
Patent number
US08969555B2

Reaction notes

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