1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67494486, compound

HRID 2047148Notes

Reaction equation

HRID 2047148 reaction equation
OC(C(F)(F)F)=O.[NH2:8][C:9]1[N:14]2[N:15]=[CH:16][C:17]([C:18]3[CH:19]=[N:20][C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:22][CH:23]=3)=[C:13]2[N:12]=[C:11]([CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[C:10]=1[C:36]#[N:37].CCN(C(C)C)C(C)C.[OH:47][C@H:48]([CH2:52][OH:53])[C:49](O)=[O:50].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C>[NH2:8][C:9]1[N:14]2[N:15]=[CH:16][C:17]([C:18]3[CH:19]=[N:20][C:21]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)=[CH:22][CH:23]=3)=[C:13]2[N:12]=[C:11]([CH:30]2[CH2:31][CH2:32][N:33]([C:49](=[O:50])[C@H:48]([OH:47])[CH2:52][OH:53])[CH2:34][CH2:35]2)[C:10]=1[C:36]#[N:37]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 439194(2R)-2,3-Dihydroxypropanoic acidHCID 86664787HCID 86664787, compound

Product 1

HCID 67494486HCID 67494486, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 7-amino-3-(6-phenylpyridin-3-yl)-5-(piperidin-4-yl)pyrazolo[1,5-a]pyrimidine-6-carbonitrile TFA salt (0.1 mmol), DIEA (87 μL, 0.5 mmol) in DMF (2 mL) was added a solution of (R)-2,3-dihydroxypropanoic acid (11 mg, 0.1 mmol), HOBt (14 mg, 0.1 mmol), EDCI (29 mg, 0.15 mmol) in DMF (1 mL). The reaction was stirred at rt for 2.5 hour and the mixture was directly purified by HPLC to furnish the title compound. LC/MS RT=2.86 min. Mass calculated for M+H 484.2, observed 484.3.

Workup

  1. customthe mixture was directly purified by HPLC

Sources & evidence

ORD record
ord-e3f363ff4e8d48948f44978dff639cc5
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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