1,2-Dichloroethane → HCID 56960961, compound

HRID 1423311Notes

Reaction equation

HRID 1423311 reaction equation
[C:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]3[CH:14]=[N:15][N:16]4[C:21]([NH2:22])=[C:20]5[CH2:23][NH:24][CH2:25][C:19]5=[N:18][C:17]=34)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:26](O)(=[O:30])[C@@H:27]([CH3:29])[OH:28].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[NH2:22][C:21]1[N:16]2[N:15]=[CH:14][C:13]([C:10]3[CH:11]=[N:12][C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[CH:8][CH:9]=3)=[C:17]2[N:18]=[C:19]2[CH2:25][N:24]([C:26](=[O:30])[C@H:27]([OH:28])[CH3:29])[CH2:23][C:20]=12

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 61503D-Lactic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66980309HCID 66980309, compound

Product 1

HCID 56960961HCID 56960961, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of crude 3-(6-phenylpyridin-3-yl)-6,7-dihydro-5H-pyrazolo[1,5-a]pyrrolo[3,4-d]pyrimidin-8-amine (0.28 mmol), D-(−)-lactic acid (33.6 mg, 0.37 mmol), EDC (109.7 mg, 0.57 mmol), HOBt (77.6 mg, 0.57 mmol) and DIEA (299.7 uL, 1.72 mmol) in DMF (4 mL) was stirred at room temperature overnight. Purification with prep-LC provided (R)-1-(8-amino-3-(6-phenylpyridin-3-yl)-5H-pyrazolo[1,5-a]pyrrolo[3,4-d]pyrimidin-6(7H)-yl)-2-hydroxypropan-1-one: LCMS tR=2.65 Min (10 min run, UV254nm), Mass calculated for, M+400.1, observed LC/MS m/z 401.1 (M+H).

Workup

  1. customPurification

Sources & evidence

ORD record
ord-5ae76f911b904a30b64e1aeebb4571af
Source dataset
uspto-grants-2015_01
Patent number
US08927562B2

Reaction notes

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