1-Hydroxybenzotriazole → HCID 178522660, compound

HRID 2102220Notes

Reaction equation

HRID 2102220 reaction equation
[CH:1]1([N:7]2[C: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)=[CH:10][C:9]([CH2:23][C:24]3[CH:32]=[CH:31][C:27]([C:28]([OH:30])=O)=[CH:26][CH:25]=3)=[N:8]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.C(Cl)CCl>[CH:1]1([N:7]2[C: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)=[CH:10][C:9]([CH2:23][C:24]3[CH:32]=[CH:31][C:27]([C:28]([NH:44][C:45]4[NH:49][N:48]=[N:47][N:46]=4)=[O:30])=[CH:26][CH:25]=3)=[N:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 67335173HCID 67335173, compoundHCID 178509300HCID 178509300, compound

Product 1

HCID 178522660HCID 178522660, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 6228DimethylformamideSolvent

Procedure

A solution of 55.6 mg product from Step E above, 28.8 mg EDC, 20.3 mg HOBt in 1 mL DMF was stirred at room temperature for 45 minutes. 5-Aminotetrazole monohydrate (15.5 mg) was added and the mixture stirred for additional 22 hours. DIEA (26 μL) and more EDC (13.8 mg) were added and the reaction continued for another day. The title compound was isolated on preparative HPLC using 75˜90% MeCN gradient over 10 minutes at 8.0 mL per minute with 0.1% TFA as a white solid following lyophilization. LC-MS: 2.26 min. (M+H=512.1).

Workup

  1. waitthe reaction continued for another day

Sources & evidence

ORD record
ord-295f9b28672c402cb1bf1522a3826a5a
Source dataset
uspto-grants-2009_08
Patent number
US07572922B2

Reaction notes

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