1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67494352, compound

HRID 2047138Notes

Reaction equation

HRID 2047138 reaction equation
[OH:1][C@H:2]([CH3:6])[C:3](O)=[O:4].CCN=C=NCCCN(C)C.ON1C2C=CC=CC=2N=N1.[NH2:28][C:29]1[N:34]2[N:35]=[CH:36][C:37]([C:38]3[CH:39]=[N:40][C:41]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)=[CH:42][CH:43]=3)=[C:33]2[N:32]=[C:31]([CH:50]2[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]2)[C:30]=1[C:56](=[O:59])[CH2:57][OH:58].C(N(CC)C(C)C)(C)C>CN(C=O)C>[NH2:28][C:29]1[N:34]2[N:35]=[CH:36][C:37]([C:38]3[CH:39]=[N:40][C:41]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)=[CH:42][CH:43]=3)=[C:33]2[N:32]=[C:31]([CH:50]2[CH2:55][CH2:54][N:53]([C:3](=[O:4])[C@H:2]([OH:1])[CH3:6])[CH2:52][CH2:51]2)[C:30]=1[C:56](=[O:59])[CH2:57][OH:58]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 61503D-Lactic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66735500HCID 66735500, compound

Product 1

HCID 67494352HCID 67494352, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (R)-2-hydroxypropanoic acid (13.8 mg, 0.16 mmol), EDCI (46 mg, 0.24 mmol), and 1-hydroxybenzotriazole (16.22 mg, 0.12 mmol) in DMF (2 ml) was stirred at room temperature for 10 min. To this 1-(7-amino-3-(6-phenylpyridin-3-yl)-5-(piperidin-4-yl)pyrazolo[1,5-a]pyrimidin-6-yl)-2-hydroxyethanone (58.77 mg, 0.12 mmol) was added followed by N,N-diisopropylethylamine (0.1 ml, 0.6 mmol). It was stirred further for 20 min at room temperature at which time LC/MS analysis confirmed full consumption of starting material. This crude compound was submitted to the analytical group for purification to afford the desired (R)-1-(4-(7-amino-6-(2-hydroxyacetyl)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperidin-1-yl)-2-hydroxypropan-1-one. LCMS: 3.27 mins, m/z=501.0 (MH+).

Workup

  1. stirringIt was stirred further for 20 min at room temperature at which time LC/MS analysis
  2. customconsumption of starting material
  3. customThis crude compound was submitted to the analytical group for purification

Sources & evidence

ORD record
ord-3a9b64550b54419a8aa194bdec905c2e
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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