Trifluoroacetic acid → HCID 24956920, compound

HRID 1714395Notes

Reaction equation

HRID 1714395 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([O:16][C:17]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:18]=3[C:19]#[N:20])[CH2:12][CH2:11]2)[CH2:4][CH2:3]1.FC(F)(F)C(O)=O.[CH:33]1([C:37](O)=[O:38])[CH2:36][CH2:35][CH2:34]1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C>CN(C)C=O>[C:19]([C:18]1[CH:21]=[C:22]([F:25])[CH:23]=[CH:24][C:17]=1[O:16][CH:13]1[CH2:12][CH2:11][N:10]([CH2:9][CH2:8][CH:5]2[CH2:6][CH2:7][CH:2]([NH:1][C:37]([CH:33]3[CH2:36][CH2:35][CH2:34]3)=[O:38])[CH2:3][CH2:4]2)[CH2:15][CH2:14]1)#[N:20]

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 19494Cyclobutanecarboxylic acidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178510120HCID 178510120, compound

Product 1

HCID 24956920HCID 24956920, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared analogously to example 1 (1.5) from Trans 2-{1-[2-(4-Amino-cyclohexyl)-ethyl]-piperidin-4-yloxy}-5-fluoro-benzonitrile; trifluoro-acetic acid salt and cyclobutanecarboxylic acid using 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyl uronium tetrafluoroborate and N-ethyldiisopropylamine in dimethylformamide (DMF). The residue was taken up on methanol and purified with preparative HPLC on reversed phase eluting with acetonitrile/water. MS (m/e): 428.0. (M+H+).

Workup

  1. custompurified with preparative HPLC on reversed phase
  2. washeluting with acetonitrile/water

Sources & evidence

ORD record
ord-127a8c3a0f164e57810162a70ba5aa3d
Source dataset
uspto-grants-2010_09
Patent number
US07795437B2

Reaction notes

Loading…