1-Hydroxybenzotriazole → HCID 178522661, compound

HRID 2102223Notes

Reaction equation

HRID 2102223 reaction equation
[CH:1]1([N:7]2[C:11]([CH2:12][C:13]3[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=3)=[CH:10][C:9]([C:22]3[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=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.CC#N.O.C(Cl)CCl>[CH:1]1([N:7]2[C:11]([CH2:12][C:13]3[CH:21]=[CH:20][C:16]([C:17]([NH:44][C:45]4[NH:49][N:48]=[N:47][N:46]=4)=[O:18])=[CH:15][CH:14]=3)=[CH:10][C:9]([C:22]3[CH:23]=[CH:24][C:25]([O:28][C:29]([F:31])([F:32])[F:30])=[CH:26][CH:27]=3)=[N:8]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

9

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 67335127HCID 67335127, compoundHCID 178509300HCID 178509300, compound

Product 1

HCID 178522661HCID 178522661, compound

Reagents, catalysts & solvents 4

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 6342AcetonitrileSolvent

Procedure

A mixture of 44.4 mg product from Step B above, 28.8 mg EDC, 20.3 mg HOBt and 13.4 mg aminotetrazole monohydrate was dissolved in 1 mL DMF. DIEA (44 μL) was added immediately and the resulting solution was stirred at room temperature for five days. The reaction mixture was diluted with a mixture of DMF, MeCN, and water and purified on preparative HPLC using 70˜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 (CD3OD, 500 MHz) δ 8.03 (d, J=8.3 Hz, 2H), 7.84˜7.86 (m, 2H), 7.46 (d, J=8.2 Hz, 2H), 7.28 (d, J=8.2 Hz, 2H), 6.47 (s, 1H), 4.23 (s, 2H), 4.055 (tt, J=3.7 & 11.7 Hz, 1H), 1.88˜1.97 (m, 2H), 1.81˜1.85 (m, 2H), 1.67˜1.73 (m, 3H), 1.25˜1.39 (m, 3H). LC-MS: 2.34 min. (M+H=512.2).

Workup

  1. custompurified on preparative HPLC
  2. customover 10 minutes

Sources & evidence

ORD record
ord-aa0b0b18a14c477c87bb980819e34a2e
Source dataset
uspto-grants-2009_08
Patent number
US07572922B2

Reaction notes

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