1-Hydroxybenzotriazole → HCID 178516355, compound

HRID 2368982Notes

Reaction equation

HRID 2368982 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]5[NH:22][CH2:23][CH2:24][C:25](=[O:26])[C:20]=5[C:19]([CH:27]5[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]5)=[N:18][C:17]=34)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:33]1[CH:37]=[N:36][C:35]([C:38](O)=[O:39])=[N:34]1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)CCl>[N:33]1[N:34]=[C:35]([C:38]([N:30]2[CH2:31][CH2:32][CH:27]([C:19]3[C:20]4[C:25](=[O:26])[CH2:24][CH2:23][NH:22][C:21]=4[N:16]4[N:15]=[CH:14][C:13]([C:10]5[CH:11]=[N:12][C:7]([C:1]6[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=6)=[CH:8][CH:9]=5)=[C:17]4[N:18]=3)[CH2:28][CH2:29]2)=[O:39])[NH:36][CH:37]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1361688203-(6-phenylpyridin-3-yl)-5-(piperidin-4-yl)-8,9-dihydropyrazolo[1,5-a]pyrido[3,2-e]pyrimidin-6(7H)-oneHCID 178524907HCID 178524907, compound

Product 1

HCID 178516355HCID 178516355, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(6-phenylpyridin-3-yl)-5-(piperidin-4-yl)-8,9-dihydropyrazolo[1,5-a]pyrido[3,2-e]pyrimidin-6(7H)-one (70 mg, 0.17 mmoL), 1H-1,2,4-triazole-3-carboxylic acid (20.5 mg, 0.18 mmoL), EDC (63 mg, 0.33 mmoL), HOBt (44.6 mg, 0.33 mmoL) and DIEA (172.2 uL, 0.99 mmoL) in DMF (3 mL) was stirred at room temperature for 2 h. Purification with prep-LC provided 5-(1-(4H-1,2,4-triazole-3-carbonyl)piperidin-4-yl)-3-(6-phenylpyridin-3-yl)-8,9-dihydropyrazolo[1,5-a]pyrido[3,2-e]pyrimidin-6(7H)-one: LCMS tR=3.15 Min (10 min run, UV254nm). Mass calculated for, M+ 519.2, observed LC/MS m/z 519.97 (M+H).

Workup

  1. customPurification

Sources & evidence

ORD record
ord-b0113471547e42eea094b58ccc592322
Source dataset
uspto-grants-2014_04
Patent number
US08703784B2

Reaction notes

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