D-Lactic Acid → HCID 178434168, compound

HRID 1913253Notes

Reaction equation

HRID 1913253 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]([CH:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)=[N:8][C:9]3[N:10]([N:11]=[CH:12][C:13]=3[C:14]3[CH:15]=[N:16][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:18][CH:19]=3)[C:5]=2[NH:4][N:3]=1.[C:32](O)(=[O:36])[C@@H:33]([CH3:35])[OH:34].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)CCl>[OH:34][C@H:33]([CH3:35])[C:32]([N:29]1[CH2:30][CH2:31][CH:26]([C:7]2[C:6]3[C:2]([CH3:1])=[N:3][NH:4][C:5]=3[N:10]3[N:11]=[CH:12][C:13]([C:14]4[CH:15]=[N:16][C:17]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)=[CH:18][CH:19]=4)=[C:9]3[N:8]=2)[CH2:27][CH2:28]1)=[O:36]

Participants

7

Reactant 4

HCID 61503D-Lactic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 178434167HCID 178434167, compound

Product 1

HCID 178434168HCID 178434168, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-methyl-6-(6-phenylpyridin-3-yl)-4-(piperidin-4-yl)-1H-dipyrazolo[1,5-a:4′,3′-e]pyrimidine (Int-9l, 42 mg, (\10 mmoL), D-(−)-lactic acid (9.3 mg, 0.10 mmoL), EDC (39.4 mg, 0.20 mmoL), HOBt (13.9 mg, 0.10 mmoL) and DIEA (89 μL, 0.51 mmoL) in DMF (4 mL) was stirred at room temperature for 2 hr. Purification with prep-LC provided (R)-2-hydroxy-1-(4-(3-methyl-6-(6-phenylpyridin-3-yl)-1H-dipyrazolo[1,5-a:4′,3′-e]pyrimidin-4-yl)piperidin-1-yl)propan-1-one (30): LCMS tR=3.07 min (10 min run, UV254nm) Mass calculated for, M+481.2, observed LC/MS m/z 482.6 (M+H).

Workup

  1. customPurification

Sources & evidence

ORD record
ord-51795269eeea4b93b2e8ba8023bebf04
Source dataset
uspto-grants-2013_12
Patent number
US08609675B2

Reaction notes

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