Diisopropylethylamine → HCID 44556111, compound

HRID 336398Notes

Reaction equation

HRID 336398 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]3[N:14]=[C:15]([NH:17][C:18]4[CH:26]=[CH:25][C:21]([C:22]([OH:24])=O)=[CH:20][CH:19]=4)[N:16]=[C:12]3[CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[NH2:60][CH:61]1[CH2:66][CH2:65][N:64](C(OC(C)(C)C)=O)[CH2:63][CH2:62]1>FC(F)(F)C(O)=O.O1CCCC1.ClCCl.O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]3[N:14]=[C:15]([NH:17][C:18]4[CH:19]=[CH:20][C:21]([C:22]([NH:60][CH:61]5[CH2:66][CH2:65][NH:64][CH2:63][CH2:62]5)=[O:24])=[CH:25][CH:26]=4)[N:16]=[C:12]3[CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59186305HCID 59186305, compound

Product 1

HCID 44556111HCID 44556111, compoundYield 17.7%

Reagents, catalysts & solvents 2

HCID 18627201HCID 18627201, compoundSolventHCID 21919333Tetrahydrofurane dichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of 4-{[5-(3-chlorophenyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino}benzoic acid (182 mg, 0.499 mmol, 1 equiv), O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (228 mg, 0.600 mmol, 1.20 equiv), and diisopropylethylamine (97 mg, 0.75 mmol, 1.5 equiv) in 1:2 dichloromethane/tetrahydrofuran (5 mL) was added tert-butyl 4-amino-1-piperidine carboxylate (120 mg, 0.60 mmol, 1.2 equiv). The resulting mixture was stirred at 30° C. overnight, filtered, concentrated to give crude product. The crude product was dissolved in 1:1 trifluoroacetic acid/tetrahydrofuran (10 ml) and stirred at room temperature for 2 h. After removal of the solvent, the resulting residue was purified by preparative HPLC to give the desired product (39.5 mg, 17%). 1H NMR (400 MHz, DMSO-d6), δ: 9.98 (s, 1H), 8.24 (s, 1H), 7.94-7.97 (m, 1H), 7.86 (s, 3H), 7.61-7.75 (m, 6H), 7.29-7.32 (m, 3H), 3.30-3.40 (m, 3H), 3.00 (m, 2H), 1.89 (m, 2H), 1.40 (m, 2H). LCMS (ESI) m/z: 447.0.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customto give crude product
  4. stirringstirred at room temperature for 2 h
  5. customAfter removal of the solvent
  6. customthe resulting residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-56e963ea16064cb3aaa9b238b31a1098
Source dataset
uspto-grants-2014_11
Patent number
US08889673B2

Reaction notes

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