Dimethylformamide → HCID 178516354, compound

HRID 2369005Notes

Reaction equation

HRID 2369005 reaction equation
[CH:1]12[NH:35][CH:5]([CH2:6][CH:7]([C:9]3[C:14]4[C:15](=[O:19])[CH2:16][CH2:17][NH:18][C:13]=4[N:12]4[N:20]=[CH:21][C:22]([C:23]5[CH:24]=[N:25][C:26]([C:29]6[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=6)=[CH:27][CH:28]=5)=[C:11]4[N:10]=3)[CH2:8]1)[CH2:4][O:3][CH2:2]2.CCN=C=NCCC[N:44]([CH3:46])C.C1C=CC2N(O)[N:54]=[N:53][C:51]=2[CH:52]=1.CCN(C(C)C)C(C)C.CN(C=[O:70])C>CS(C)=O.CC#N.O>[NH:54]1[CH:46]=[N:44][C:51]([C:52]([N:35]2[C@H:1]3[CH2:8][CH:7]([C:9]4[C:14]5[C:15](=[O:19])[CH2:16][CH2:17][NH:18][C:13]=5[N:12]5[N:20]=[CH:21][C:22]([C:23]6[CH:24]=[N:25][C:26]([C:29]7[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=7)=[CH:27][CH:28]=6)=[C:11]5[N:10]=4)[CH2:6][C@@H:5]2[CH2:4][O:3][CH2:2]3)=[O:70])=[N:53]1

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 136404757HCID 136404757, compound2×

Product 1

HCID 178516354HCID 178516354, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22251437Acetonitrile dimethylsulfoxideSolvent

Procedure

5-(3-oxa-9-azabicyclo[3.3.1]nonan-7-yl)-3-(6-phenylpyridin-3-yl)-8,9-dihydropyrazolo[1,5-a]pyrido[3,2-e]pyrimidin-6(7H)-one (49.78 mg, 0.44 mmol) in DMF (2 mL) was treated with EDCI (129.47 mg, 0.678 mmol) and HOBt (45.6 mg, 0.339 mmol). Then substrate 5-(3-oxa-9-azabicyclo[3.3.1]nonan-7-yl)-3-(6-phenylpyridin-3-yl)-8,9-dihydropyrazolo[1,5-a]pyrido[3,2-e]pyrimidin-6(7H)-one (122 mg, 0.21 mmol) followed by DIEA (0.29 mL, 1.69 mmol) was added. After 30 min, the reaction mixture was treated with water (0.4 mL) and DMSO-MeCN (3:1, 3 mL). Pure compound 5-((1R,5S)-9-(1H-1,2,4-triazole-3-carbonyl)-3-oxa-9-azabicyclo[3.3.1]nonan-7-yl)-3-(6-phenylpyridin-3-yl)-8,9-dihydropyrazolo[1,5-a]pyrido[3,2-e]pyrimidin-6(7H)-one was isolated by preparative HPLC. HPLC-MS tR=4.35 min (UV254 nm). Mass calculated for formula C30H27N9O3 561.2; observed MH+ (LCMS) 561.98 (m/z).

Workup

  1. additionwas added

Sources & evidence

ORD record
ord-1bbbd2ef68ff4a99bfa13bc131eacd78
Source dataset
uspto-grants-2014_04
Patent number
US08703784B2

Reaction notes

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