Trifluoroacetic acid → HCID 11342085, compound

HRID 970102Notes

Reaction equation

HRID 970102 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][C:18]2[N:21]([CH2:31][CH:32]([OH:48])[CH2:33][N:34]3[CH2:39][CH2:38][N:37]([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=4[C:46]#[N:47])[CH2:36][CH2:35]3)[N:22]=[C:23]([C:24]3[CH:29]=[CH:28][C:27]([I:30])=[CH:26][CH:25]=3)[C:17]=2[CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[OH:48][CH:32]([CH2:31][N:21]1[C:18]2[CH2:19][CH2:20][NH:15][CH2:16][C:17]=2[C:23]([C:24]2[CH:29]=[CH:28][C:27]([I:30])=[CH:26][CH:25]=2)=[N:22]1)[CH2:33][N:34]1[CH2:35][CH2:36][N:37]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[C:46]#[N:47])[CH2:38][CH2:39]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10146441HCID 10146441, compound

Product 1

HCID 11342085HCID 11342085, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (3 mL) was added to a solution of 1-{3-[4-(2-cyano-phenyl)-piperazin-1-yl]-2-hydroxy-propyl}-3-(4-iodo-phenyl)-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridine-5-carboxylic acid tert-butyl ester (0.402 g, 0.601 mmol) in CH2Cl2 (3 mL) and the reaction mixture was stirred for 2 h. The mixture was concentrated, then diluted with EtOAc. The organic layer was washed with aqueous NaHCO3 and brine, dried (Na2SO4), and concentrated to afford the amine (0.342 g, 100%) as a yellowish foam. TLC (silica, 10% acetone/CH2Cl2): Rf=0.14. MS (electrospray): m/z 569.2 (569.1, calculated for C26H29IN6O, [M+H]+). 1H NMR (400 MHz, CDCl3:CD3OD(6:1)): 7.73 (d, J=8.6 Hz, 2H), 7.56 (dd, J=7.6, 1.8 Hz, 1H), 7.52 (t, J=8.0 Hz, 1H), 7.25 (d, J=8.6 Hz, 2H), 7.09 (t, J=7.6 Hz, 1H), 7.02 (dd, J=8.4 Hz, 1H), 4.43-4.36 (m, 1H), 4.31 (s, 2H), 4.21 (dd, J=14.1, 4.5 Hz, 1H), 4.11 (dd, J=14.5, 6.3 Hz, 1H), 3.54-3.49 (m, 2H), 3.40-3.24 (m, 8H), 3.18-3.06 (m, 3H), 3.03-2.95 (m, 3H).

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with EtOAc
  3. washThe organic layer was washed with aqueous NaHCO3 and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3cb2e8cf5e9e4e608cfc97a4ea4f3e5c
Source dataset
uspto-grants-2007_12
Patent number
US07309703B2

Reaction notes

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