Diisopropylethylamine → HCID 69087553, compound

HRID 2173460Notes

Reaction equation

HRID 2173460 reaction equation
OC(C(F)(F)F)=O.[CH:8]12[CH2:14][CH:13]1[NH:12][CH2:11][CH2:10][N:9]2[CH2:15][C@@H:16]([C:18]1[CH:27]=[CH:26][C:21]2[C:22](=[O:25])[O:23][CH2:24][C:20]=2[C:19]=1[CH3:28])[OH:17].CCN(C(C)C)C(C)C.[N:38]1([C:43]2[N:48]=[CH:47][C:46]([CH2:49][C:50](O)=[O:51])=[CH:45][CH:44]=2)[CH:42]=[N:41][N:40]=[N:39]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[OH:17][C@H:16]([C:18]1[CH:27]=[CH:26][C:21]2[C:22](=[O:25])[O:23][CH2:24][C:20]=2[C:19]=1[CH3:28])[CH2:15][N:9]1[CH2:10][CH2:11][N:12]([C:50](=[O:51])[CH2:49][C:46]2[CH:47]=[N:48][C:43]([N:38]3[CH:42]=[N:41][N:40]=[N:39]3)=[CH:44][CH:45]=2)[CH:13]2[CH:8]1[CH2:14]2

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66524945[6-(1H-Tetrazol-1-yl)pyridine-3-yl]acetic acidHCID 131732971HCID 131732971, compound

Product 1

HCID 69087553HCID 69087553, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In a round bottom flask, 5-{(1R)-2-[(±)-2,5-diazabicyclo[4.1.0]hept-2-yl]-1-hydroxyethyl}-4-methyl-2-benzofuran-1(3H)-one TFA salt (66 mg, 0.126 mmol) was dissolved in DMF (2 mL). DIEA (66 mg, 0.511 mmol) was added, followed by [6-(1H-tetrazol-1-yl)pyridin-3-yl]acetic acid (32 mg, 0.153 mmol). HATU (73 mg, 0.192 mmol) was added and let reaction stir at room temperature for 6 hours. Then reaction was diluted by adding small amount of water and was put on prep-HPLC for purification (Sunfire-C18 column, eluted by 10-75% AcCN/H2O+0.1% formic acid). Lyophilization gave the title compound. 1H NMR (ppm) (500 MHz, CD3OD): δ 9.90 (1H, s), 8.50 (1H, s), 8.07-8.00 (2H, m), 7.80 (1H, m), 7.72 (1H, d, J=8.0 Hz), 5.36 (2H, d, J=3.10 Hz), 5.40-5.31 (1H, m), 4.10 (2H, s), 4.08-3.95 (1H, m), 3.20-3.07 (1H, in), 3.06-2.83 (3H, m), 2.80 (2H, s), 2.78-2.68 (2H, m), 2.54-2.39 (1H, m), 2.36 (3H, s), 0.95 (1H, t, J=6.39 Hz), 0.81 (1H, t, J=4.98 Hz); LC/MS: (M+23)+ =498.

Workup

  1. customreaction
  2. customThen reaction
  3. additionwas diluted
  4. customprep-HPLC for purification (Sunfire-C18 column, eluted by 10-75% AcCN/H2O+0.1% formic acid)

Sources & evidence

ORD record
ord-6d92aa1f465944fabe4bb117b4a4ad16
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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