1-Hydroxybenzotriazole → HCID 178516353, compound

HRID 2368970Notes

Reaction equation

HRID 2368970 reaction equation
[CH:1]12[NH:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][CH:3]([C:9]1[C:14]3[C:15](=[O:19])[CH2:16][CH2:17][NH:18][C:13]=3[N:12]3[N:20]=[CH:21][C:22]([C:23]4[CH:24]=[N:25][C:26]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)=[CH:27][CH:28]=4)=[C:11]3[N:10]=1)[CH2:2]2.[NH:35]1[CH:39]=[N:38][C:37]([C:40](O)=[O:41])=[N:36]1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)CCl>[N:35]1[N:36]=[C:37]([C:40]([N:8]2[CH:1]3[CH2:7][CH2:6][CH:5]2[CH2:4][CH:3]([C:9]2[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:30]=[CH:31][CH:32]=[CH:33][CH:34]=6)=[CH:27][CH:28]=5)=[C:11]4[N:10]=2)[CH2:2]3)=[O:41])[NH:38][CH:39]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 136404759HCID 136404759, compoundHCID 178524907HCID 178524907, compound

Product 1

HCID 178516353HCID 178516353, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-(8-azabicyclo[3.2.1]octan-3-yl)-3-(6-phenylpyridin-3-yl)-8,9-dihydropyrazolo[1,5-a]pyrido[3,2-e]pyrimidin-6(7H)-one (86 mg, 0.19 mmoL), 1H-1,2,4-triazole-3-carboxylic acid (25.9 mg, 0.23 mmoL), EDC (73 mg, 0.38 mmoL), HOBt (51.6 mg, 0.38 mmoL) and DIEA (199 uL, 1.15 mmoL) in DMF (4 mL) was stirred at room temperature for 2 h. Purification with prep-LC provided 5-(8-(4H-1,2,4-triazole-3-carbonyl)-8-azabicyclo[3.2.1]octan-3-yl)-3-(6-phenylpyridin-3-yl)-8,9-dihydropyrazolo[1,5-a]pyrido[3,2-e]pyrimidin-6(7H)-one: LCMS tR=2.33 Min (10 min run, UV254nm). Mass calculated for, M+ 545.2, observed LC/MS m/z 546.01 (M+H).

Workup

  1. customPurification

Sources & evidence

ORD record
ord-e2dcd194197544b7b914b80009475c70
Source dataset
uspto-grants-2014_04
Patent number
US08703784B2

Reaction notes

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