1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67494475, compound

HRID 2047132Notes

Reaction equation

HRID 2047132 reaction equation
Cl.[NH2:2][C:3]1[N:8]2[N:9]=[CH:10][C:11]([C:12]3[CH:13]=[N:14][C:15]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:16][CH:17]=3)=[C:7]2[N:6]=[C:5]([CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[C:4]=1[C:30](=[O:32])[CH3:31].CCN(C(C)C)C(C)C.[C:42](O)(=[O:46])[C@@H:43]([CH3:45])[OH:44].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C>[C:30]([C:4]1[C:5]([CH:24]2[CH2:25][CH2:26][N:27]([C:42](=[O:46])[C@H:43]([OH:44])[CH3:45])[CH2:28][CH2:29]2)=[N:6][C:7]2[N:8]([N:9]=[CH:10][C:11]=2[C:12]2[CH:13]=[N:14][C:15]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[CH:16][CH:17]=2)[C:3]=1[NH2:2])(=[O:32])[CH3:31]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide2×HCID 61503D-Lactic Acid2×HCID 757711-Hydroxybenzotriazole2×HCID 81531DiisopropylethylamineHCID 66737987HCID 66737987, compound

Product 1

HCID 67494475HCID 67494475, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a solution of 1-(7-amino-3-(6-phenylpyridin-3-yl)-5-(piperidin-4-yl)pyrazolo[1,5-a]pyrimidin-6-yl)ethanone hydrochloride (0.5 mmol), DIEA (350 μL, 2 mmol) in DMF (5 mL) was added a solution of D-lactic acid (45 mg, 0.5 mmol), HOBt (68 mg, 0.5 mmol), EDCI (144 mg, 0.75 mmol) in DMF (1 mL). The reaction was stirred at rt for 20 min. Another solution of solution of D-lactic acid (45 mg, 0.5 mmol), HOBt (68 mg, 0.5 mmol), EDCI (144 mg, 0.75 mmol) in DMF (2 mL) was added and stirred for 5 minutes. LC-MS indicated the reaction was complete and reaction mixture was directly purified by HPLC to furnish the title compound.

Workup

  1. stirringstirred for 5 minutes
  2. customreaction mixture
  3. customwas directly purified by HPLC

Sources & evidence

ORD record
ord-50e7ca77c31544fdad79a78c52316d99
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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