1-Hydroxybenzotriazole → HCID 178522664, compound

HRID 2102230Notes

Reaction equation

HRID 2102230 reaction equation
[CH:1]1([C:7]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=3)[N:10]=[CH:9][C:8]=2[CH2:23][C:24]2[CH:32]=[CH:31][C:27]([C:28]([OH:30])=O)=[CH:26][CH:25]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1C=CC2N(O)N=NC=2C=1.O.[NH2:44][C:45]1[NH:49][N:48]=[N:47][N:46]=1.CCN(C(C)C)C(C)C>CN(C=O)C.CS(C)=O.CC#N.O.C(Cl)CCl>[CH:1]1([C:7]2[N:11]([C:12]3[CH:13]=[CH:14][C:15]([O:18][C:19]([F:20])([F:22])[F:21])=[CH:16][CH:17]=3)[N:10]=[CH:9][C:8]=2[CH2:23][C:24]2[CH:25]=[CH:26][C:27]([C:28]([NH:44][C:45]3[NH:49][N:48]=[N:47][N:46]=3)=[O:30])=[CH:31][CH:32]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

10

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 67334871HCID 67334871, compoundHCID 178509300HCID 178509300, compound

Product 1

HCID 178522664HCID 178522664, compound

Reagents, catalysts & solvents 5

HCID 111,2-DichloroethaneSolventHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 66.7 mg product from Step F above, 71.9 mg EDC, 30.4 mg HOBt and 23.2 mg aminotetrazole monohydrate was dissolved in 1 mL DMF. DIEA (92 μL) was added immediately and the resulting solution was stirred at room temperature for 17 hours. The reaction mixture was diluted with a mixture of DMSO, MeCN, and water and purified on preparative HPLC using 65˜80% MeCN gradient over 10 minutes at 8.0 mL per minute with 0.1% TFA. The title compound was obtained as a white solid following lyophilization. 1H NMR (DMSO-d6, 500 MHz) δ 8.045 (d, J=8.2 Hz, 2H), 7.50˜7.54 (m, 4H), 7.41 (d, J=8.2 Hz, 2H), 7.33 (s, 1H), 4.06 (s, 2H), 2.64 (tt, J=3.0 & 12.2 Hz, 1H), 1.62˜1.72 (m, 4H), 1.48˜1.48 (m, 3H), 1.05˜1.15 (m, 3H). LC-MS: 1.97 min. (M+H=512.2).

Workup

  1. custompurified on preparative HPLC
  2. customover 10 minutes

Sources & evidence

ORD record
ord-bac9d64912a7454ca7fcc83d41e2fb09
Source dataset
uspto-grants-2009_08
Patent number
US07572922B2

Reaction notes

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