Triethylamine → HCID 44178168, compound

HRID 340408Notes

Reaction equation

HRID 340408 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:23][CH2:22][C:11]3[NH:12][C:13]4[CH:14]=[CH:15][C:16]([C:19]([OH:21])=O)=[CH:17][C:18]=4[C:10]=3[CH2:9]2)=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.Cl.[N:50]1[CH:55]=[CH:54][CH:53]=[C:52]([CH2:56][N:57]2[CH2:62][CH2:61][CH:60]([NH2:63])[CH2:59][CH2:58]2)[CH:51]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:23][CH2:22][C:11]3[NH:12][C:13]4[CH:14]=[CH:15][C:16]([C:19]([NH:63][CH:60]5[CH2:59][CH2:58][N:57]([CH2:56][C:52]6[CH:51]=[N:50][CH:55]=[CH:54][CH:53]=6)[CH2:62][CH2:61]5)=[O:21])=[CH:17][C:18]=4[C:10]=3[CH2:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 51051977HCID 51051977, compoundHCID 57750062HCID 57750062, compound

Product 1

HCID 44178168HCID 44178168, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-fluorophenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxylic acid (24, 50 mg, 0.16 mmol) in DMF (2.0 mL), HATU (75 mg, 0.2 mmol), 1-(pyridin-3-ylmethyl)piperidin-4-amine dihydrochloride (48 mg, 0.16 mmol) and triethylamine (150 μL, 110 mg, 1.1 mmol) were added. The resulting reaction mixture was allowed to stir at room temperature overnight, poured into saturated sodium bicarbonate solution (10 mL) to give a precipitate, filtered and dried under vacuum overnight. Trituration with ethyl ether provided 2-(4-fluorophenyl)-N-(1-(pyridin-3-ylmethyl)piperidin-4-yl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxamide (Compound 36) as a pale yellow solid (57 mg, 73%). 1H NMR (DMSO-d6, 300 MHZ) 11.08 (s, 1H), 8.49 (d, J=1.4 Hz, 1H), 8.45 (dd, J=4.8, 1.5 Hz, 1H), 8.03 (d, J=8.0 Hz, 1H), 8.02 (s, 1H), 7.70 (dt, J=7.7, 1.8 Hz, 1H), 7.56 (dd, J=8.4, 1.5 Hz, 1H), 7.35 (dd, J=7.7, 4.7 Hz, 1H), 7.28 (d, J=8.3 Hz, 1H), 7.06 (d, J=5.0 Hz, 2H), 7.05 (d, J=3.3 Hz, 2H), 4.37 (s, 2H), 3.87-3.72 (m, 1H), 3.63 (t, J=5.2 Hz, 2H), 3.52 (s, 2H), 2.92-2.78 (m, 4H), 2.12-2.00 (m, 2H), 1.80 (d, J=10.5 Hz, 2H), 1.61 (qd, J=11.7, 3.0 Hz, 2H) ppm; MS (ES) 484 (M+H).

Workup

  1. customThe resulting reaction mixture
  2. customto give a precipitate
  3. filtrationfiltered
  4. customdried under vacuum overnight

Sources & evidence

ORD record
ord-cb7b4de18c9a47469e7df2869c1241f7
Source dataset
uspto-grants-2014_11
Patent number
US08895578B2

Reaction notes

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