Diisopropylethylamine → HCID 178520680, compound

HRID 870617Notes

Reaction equation

HRID 870617 reaction equation
Cl.CN(C)CCCN=C=NCC.C(N(C(C)C)CC)(C)C.[N:22]1[NH:23][N:24]=[C:25]([O:27][CH2:28][CH2:29][CH2:30][C:31]([OH:33])=O)[CH:26]=1.O.Cl.Cl.[CH2:37]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:39][CH:38]1[NH:46][C:47]1[N:48]=[CH:49][C:50]2[CH2:55][NH:54][CH2:53][C:51]=2[N:52]=1>CN(C)C1C=CN=CC=1.ClCCl>[CH2:39]1[C:40]2[C:45](=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH2:37][CH:38]1[NH:46][C:47]1[N:48]=[CH:49][C:50]2[CH2:55][N:54]([C:31](=[O:33])[CH2:30][CH2:29][CH2:28][O:27][C:25]3[NH:24][N:23]=[N:22][CH:26]=3)[CH2:53][C:51]=2[N:52]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86726534N-(2,3-dihydro-1H-inden-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-amine dihydrochloride hydrateHCID 867265814-(2H-triazol-4-yloxy)butanoic acid

Product 1

HCID 178520680HCID 178520680, compoundYield 44.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Add 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.168 g; 1.5 equiv; 0.88 mmoles) and diisopropylethylamine (0.41 mL; 4 equiv; 2.34 mmoles) to a solution of 4-(2H-triazol-4-yloxy)butanoic acid (0.1 g; 1.0 equiv; 0.58 mmoles) and N-(2,3-dihydro-1H-inden-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-amine dihydrochloride hydrate (0.201 g; 1.0 equiv; 0.58 mmoles), and N,N-dimethyl-4-pyridinamine, (0.014 g; 0.2 equiv; 0.12 mmoles) in dichloromethane (5.8 mL). Stir the reaction for 2 hours then load the reaction mixture directly onto a silica gel column. Purify by column chromatography (10% (2 N ammonia in methanol)/ethyl acetate) to afford 1-[2-(2,3-dihydro-1H-inden-2-ylamino)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidin-6-yl]-4-(1H-1,2,3-triazol-5-yloxy)butan-1-one (0.104 g; 44%) as a white solid: MS (m/z): 406(M+1).

Workup

  1. customthe reaction for 2 hours
  2. customPurify by column chromatography (10% (2 N ammonia in methanol)/ethyl acetate)

Sources & evidence

ORD record
ord-cd3edb7680e0407b865339a14e8086b2
Source dataset
uspto-grants-2015_03
Patent number
US08969555B2

Reaction notes

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