Triethylamine → HCID 66739507, compound

HRID 1641023Notes

Reaction equation

HRID 1641023 reaction equation
[CH:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5]1)([CH3:3])[CH3:2].[C:13](Cl)(=[O:17])[C:14]([Cl:16])=[O:15].[N:19]1([CH2:25][CH2:26][CH2:27][NH2:28])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.C(N(CC)CC)C>C(OCC)C.C1COCC1>[ClH:16].[CH:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13](=[O:17])[C:14]([NH:28][CH2:27][CH2:26][CH2:25][N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:15])=[CH:5]1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 19049Piperidine-1-propylamineHCID 65578Oxalyl chlorideHCID 4389257HCID 4389257, compound

Product 1

HCID 66739507HCID 66739507, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared according to general procedure B described in Scheme 1. A solution of N-isopropylindole (480 mg, 3 mmol) in diethylether (10 mL) was cooled to 0° C. and treated dropwise with oxalyl chloride (303 μL, 3.5 mmol). The reaction was gradually warmed to RT over a 3 h period affording a yellow precipitate. The reaction mixture was concentrated under reduced pressure and the resulting yellow solid was dissolved in DCM (15 mL), cooled to 0° C. and treated with a solution of 1-piperidinepropanamine (313 g, 2 mmol) and triethylamine (334 μL, 2.4 mmol) in THF (10 mL). The reaction mixture was allowed to warm to RT and stirred for 14 h. The reaction mixture was concentrated under reduced pressure and the crude material was purified on silica gel (Biotage, 0-30% MeOH/DCM) and then converted to the HCl salt to provide the title compound as a purple solid (112 mg, 100% yield). 1H NMR (400 MHz, CDCl3): δ 12.19 (NH+, br s, 1H), 9.02 (s, 1H), 8.44 (dd, 1H), 7.95 (br t, 1H), 7.44 (m, 1H), 7.33 (m, 2H), 4.71 (m, 1H), 3.54 (m, 4H), 3.00 (m, 2H), 2.59 (m, 2H), 2.29 (m, 4H), 1.9-1.7 (m, 3H), 1.61 (d, 6H) 1.39 (m, 1H); MS (ESI) m/z: Calculated for C21H29N3O2: 355.2. Found: 356.3 (M+H)+.

Workup

  1. customThe title compound was prepared
  2. customaffording a yellow precipitate
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. dissolutionthe resulting yellow solid was dissolved in DCM (15 mL)
  5. temperaturecooled to 0° C.
  6. temperatureto warm to RT
  7. concentrationThe reaction mixture was concentrated under reduced pressure
  8. customthe crude material was purified on silica gel (Biotage, 0-30% MeOH/DCM)

Sources & evidence

ORD record
ord-51c3ba0cd1c2496a8d4b439a203f9ad5
Source dataset
uspto-grants-2012_02
Patent number
US08114894B2

Reaction notes

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