Diisopropylethylamine → HCID 178513012, compound

HRID 495128Notes

Reaction equation

HRID 495128 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8][CH2:9][CH2:10][O:11][C:12]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[O:15][C:14](=[O:22])[CH:13]=1.C(N(C(C)C)CC)(C)C.C(OC([NH:39][C:40](N1C=CC=N1)=[N:41]C(OC(C)(C)C)=O)=O)(C)(C)C>C(#N)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[O:22]=[C:14]1[CH:13]=[C:12]([O:11][CH2:10][CH2:9][NH:8][C:40]([NH2:41])=[NH:39])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[O:15]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 4428040N,N'-Bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidineHCID 86035757HCID 86035757, compound

Product 1

HCID 178513012HCID 178513012, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-(2-Amino-ethoxy)-1-benzopyran-2-one trifluoroacetate (0.313 mmol, 100 mg) is placed in a small vial along with 2 mL of acetonitrile. Diisopropylethylamine is added dropwise until the pH of the solution is ˜9 by pH paper. N,N′-Bis(tert-butoxycarbonyl)-1-H-pyrazole-1-carboxamidine (0.24 mmol, 74.5 mg) is added and the reaction is mixed at ambient temperature for 5 hrs. The reaction mixture is concentrated in vacuo, then is redissolved in neat TFA and is stirred at ambient temperature for 30 min. The TFA is removed under reduced pressure and the residue is purified by reversed-phase HPLC to afford the title compound as the trifluoroacetic acid salt (35.0 mg, 31%). 1H NMR (DMSO-d6, 300 MHz) δ 7.88 (1H, dd, J=1.5, 8 Hz), 7.81 (1H, br t), 7.68 (1H, m), 7.39 (2H, m), 7.28 (3H, br s), 5.49 (1H, s), 4.30 (2H, t, J=5 Hz), 3.67 (2H, q, J=5.5 Hz); MS (ESI, Pos.) calcd for C12H13N3O3 m/z [M+H]=248.1, found 248.1.

Workup

  1. additionthe reaction is mixed at ambient temperature for 5 hrs
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. dissolutionis redissolved in neat TFA
  4. customThe TFA is removed under reduced pressure
  5. customthe residue is purified by reversed-phase HPLC

Sources & evidence

ORD record
ord-6dacdfee4fcd42ee881e2f44c3fccece
Source dataset
uspto-grants-2009_05
Patent number
US07538233B2

Reaction notes

Loading…