D-Lactic Acid → HCID 67494424, compound

HRID 2047176Notes

Reaction equation

HRID 2047176 reaction equation
[NH2:1][C:2]1[N:7]2[N:8]=[CH:9][C:10]([C:11]3[CH:12]=[N:13][C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:15][CH:16]=3)=[C:6]2[N:5]=[C:4]([O:23][CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[C:3]=1[C:30](=[O:32])[CH3:31].[C:33](O)(=[O:37])[C@@H:34]([CH3:36])[OH:35].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)CCl>[C:30]([C:3]1[C:4]([O:23][CH:24]2[CH2:25][CH2:26][N:27]([C:33](=[O:37])[C@H:34]([OH:35])[CH3:36])[CH2:28][CH2:29]2)=[N:5][C:6]2[N:7]([N:8]=[CH:9][C:10]=2[C:11]2[CH:12]=[N:13][C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:15][CH:16]=2)[C:2]=1[NH2:1])(=[O:32])[CH3:31]

Participants

7

Reactant 4

HCID 61503D-Lactic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 67494339HCID 67494339, compound

Product 1

HCID 67494424HCID 67494424, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(7-amino-3-(6-phenylpyridin-3-yl)-5-(piperidin-4-yloxy)pyrazolo[1,5-a]pyrimidin-6-yl)ethanone (211 mg, 0.49 mmoL), D-(−)-lactic acid (53.3 mg, 0.59 mmoL), EDC (189.0 mg, 0.99 mmoL), HOBt (132.0 mg, 0.99 mmoL) and DIEA (514 uL, 2.96 mmoL) in DMF (5 mL) was stirred at room temperature for 2 hr. Purification with prep-LC provided

Workup

  1. customPurification
  2. customwith prep-LC provided

Sources & evidence

ORD record
ord-865f7b7eb740410eb30e2dd2ccaa64fb
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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