D-Lactic Acid → HCID 67494492, compound

HRID 2047174Notes

Reaction equation

HRID 2047174 reaction equation
[Br:1][C:2]1[C:3]([O:24][CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[N:4][C:5]2[N:6]([N:9]=[CH:10][C:11]=2[C:12]2[CH:13]=[N:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:16][CH:17]=2)[C:7]=1[NH2:8].[C:31](O)(=[O:35])[C@@H:32]([CH3:34])[OH:33].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)CCl>[NH2:8][C:7]1[N:6]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:5]2[N:4]=[C:3]([O:24][CH:25]2[CH2:30][CH2:29][N:28]([C:31](=[O:35])[C@H:32]([OH:33])[CH3:34])[CH2:27][CH2:26]2)[C:2]=1[Br:1]

Participants

7

Reactant 4

HCID 61503D-Lactic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66733864HCID 66733864, compound

Product 1

HCID 67494492HCID 67494492, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of the crude 6-bromo-3-(6-phenylpyridin-3-yl)-5-(piperidin-4-yloxy)pyrazolo[1,5-a]pyrimidin-7-amine, D-(−)-lactic acid (18.5 mg, 0.20 mmoL), EDC (78.7 mg, 0.41 mmoL), HOBt (27.7 mg, 0.20 mmoL) and DIEA (238 uL, 1.37 mmoL) in DMF (4 mL) was stirred at room temperature for 2 hr. Purification with prep-LC provided (R)-1-(4-(7-amino-6-bromo-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yloxy)piperidin-1-yl)-2-hydroxypropan-1-one, LCMS tR=4.39 Min (10 min run, UV254nm). Mass calculated for, M+ 513.0, observed LC/MS m/z 514.43 (M+H).

Workup

  1. customPurification

Sources & evidence

ORD record
ord-4f6e3daeaaaa438e9546715feea33f73
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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