1H-Indole-7-carboxylic acid → HCID 18723510, compound

HRID 842230Notes

Reaction equation

HRID 842230 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH:15]3[CH:19]([C:20]([F:23])([F:22])[F:21])[CH2:18][NH:17][CH2:16]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[NH:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][C:31]=2[C:33](O)=[O:34])[CH:26]=[CH:25]1.Cl.CN(C)CCCN=C=NCC>CN(C1C=CN=CC=1)C.C(Cl)Cl>[NH:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][C:31]=2[C:33]([N:17]2[CH2:18][CH:19]([C:20]([F:21])([F:23])[F:22])[CH:15]([CH2:14][N:11]3[CH2:12][CH2:13][CH:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[CH2:9][CH2:10]3)[CH2:16]2)=[O:34])[CH:26]=[CH:25]1

Participants

6

Reactant 3

HCID 742811H-Indole-7-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18388387HCID 18388387, compound

Product 1

HCID 18723510HCID 18723510, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 0.12 g (0.36 mmol) of 3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(RS)-(trifluoromethyl)pyrrolidine, 0.069 g (0.43 mmol) of indole-7-carboxylic acid, 0.088 g (0.72 mmol) of DMAP and 0.097 g (0.5 mmol) of 1-[3-(Dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (Aldrich) in 10 mL of CH2Cl2 was stirred at rt for 4 h. The reaction mixture was concentrated and the residue was purified by chromatography (silica, acetone:hexanes, 1:5) to give the title compound. 1H NMR (key peaks) (CDCl3) δ9.96 (s, 1H), 7.82 (d, 1H, J=8.0 Hz), 7.44 (d, 1H, J=7.5 Hz), 7.32 (t, 1H, J=3.0 Hz), 7.17-7.21 (m, 3H), 7.03 (t, t, 2H, J=8.5 Hz), 6.62-6.63 (m, 1H); Mass Spectrum (ESI) m/e=474 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by chromatography (silica, acetone:hexanes, 1:5)

Sources & evidence

ORD record
ord-4f94d6637c544783ac75018aa83a8b48
Source dataset
uspto-grants-2002_04
Patent number
US06372764B1

Reaction notes

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