Cyclopentanecarboxylic acid → HCID 57406017, compound

HRID 1520052Notes

Reaction equation

HRID 1520052 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH:23]1([C:28]([OH:30])=O)[CH2:27][CH2:26][CH2:25][CH2:24]1.[NH:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:33]([C:40]2[N:41]=[N:42][N:43]([C:45]3[CH:50]=[CH:49][C:48]([CH2:51][NH2:52])=[CH:47][CH:46]=3)[CH:44]=2)=[N:32]1.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[NH:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:33]([C:40]2[N:41]=[N:42][N:43]([C:45]3[CH:50]=[CH:49][C:48]([CH2:51][NH:52][C:28]([CH:23]4[CH2:24][CH2:25][CH2:26][CH2:27]4)=[O:30])=[CH:47][CH:46]=3)[CH:44]=2)=[N:32]1

Participants

7

Reactant 4

HCID 18840Cyclopentanecarboxylic acidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67981038HCID 67981038, compound

Product 1

HCID 57406017HCID 57406017, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

TBTU (185 mg; 0.58 mmol; 1.3 eq.) was added to a cooled (0° C.) solution of cyclopentane carboxylic acid (53 μl; 0.49 mmol; 1.1 eq.) in DMF (2.9 mL). After 10 min, a solution of 1-{4-[4-(1H-indazol-3-yl)-1H-1,2,3-triazol-1-yl]phenyl}methanamine (145 mg; 0.44 mmol; 1.0 eq.) and DIEA (174 μl; 1.02 mmol; 2.3 eq.) in DMF (2.9 mL) was added and the reaction mixture was stirred overnight at RT. DCM was added and the reaction mixture was washed with an aqueous saturated solution of NH4Cl and brine. The organic layer was dried over magnesium sulfate, filtered and concentrated. The crude was purified by preparative HPLC to afford the title compound as a white solid. 1H NMR (300 Mz, DMSO-d 6) δ: 13.36 (brs, 1H), 9.28 (s, 1H), 8.41 (t, J=6.0 Hz, 1H), 8.36 (dt, J=8.2 Hz, 1.0 Hz, 1H), 8.00 (d, J=8.6 Hz, 2H), 7.60 (dt, J=8.2 Hz, 1.0 Hz, 1H), 7.49-7.41 (m, 3H); 7.28-7.23 (m, 1H), 4.35 (d, J=6.0 Hz, 2H), 2.70-2.59 (m, 1H), 1.84-1.49 (m, 8H). HPLC (Condition A): Rt 3.59 min (purity 97.6%). MS (ESI+): 387.3, MS (ESI−): 385.4.

Workup

  1. washthe reaction mixture was washed with an aqueous saturated solution of NH4Cl and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude was purified by preparative HPLC

Sources & evidence

ORD record
ord-7d1d2d5f836246f0a73b11cda2518042
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

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