Triethylamine → tert-butyl 5-[5-[2-(indan-2-ylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl]-5-oxo-pentyl]imidazole-1-carboxylate

HRID 870584Notes

Reaction equation

Cl.CN(C)CCCN=C=NCC.[C:13]([O:17][C:18]([N:20]1[C:24]([CH2:25][CH2:26][CH2:27][CH2:28][C:29]([OH:31])=O)=[CH:23][N:22]=[CH:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].[CH2:32]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:34][CH:33]1[NH:41][C:42]1[N:43]=[CH:44][C:45]2[CH2:51][NH:50][CH2:49][CH2:48][C:46]=2[N:47]=1.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>ClCCl>[CH2:32]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:34][CH:33]1[NH:41][C:42]1[N:43]=[CH:44][C:45]2[CH2:51][N:50]([C:29](=[O:31])[CH2:28][CH2:27][CH2:26][CH2:25][C:24]3[N:20]([C:18]([O:17][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:19])[CH:21]=[N:22][CH:23]=3)[CH2:49][CH2:48][C:46]=2[N:47]=1

Participants

Conditions

Temperature: 40 °C

Procedure

Add 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.092 g; 1.5 equiv; 0.48 mmoles) to a solution of 5-(3-tert-butoxycarbonylimidazol-4-yl)pentanoic acid (0.084 g; 1.0 equiv; 0.31 mmoles), N-indan-2-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine (0.064 g; 0.77 equiv; 0.24 mmoles), 1-hydroxybenzotriazole (0.065 g; 1.5 equiv; 0.48 mmoles), and triethylamine (0.20 mL; 4.5 equiv; 1.44 mmoles) in dichloromethane (15 mL). Heat the mixture to 40° C. for 16 hours. Concentrate the mixture, and then purify the crude product by column chromatography (0 to 10% methanol in dichloromethane) to afford tert-butyl 5-[5-[2-(indan-2-ylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl]-5-oxo-pentyl]imidazole-1-carboxylate (0.040 g; 25%) as a white solid: MS (m/z): 517 (M+1).

Workup

concentrationConcentrate the mixture
custompurify the crude product by column chromatography (0 to 10% methanol in dichloromethane)

Sources & evidence

ORD record: ord-967b197d62684d27b99a47e47a7e693e
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969555B2

Reaction notes

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