Triethylamine → but-2-ynyl 4-(1'-(dimethylcarbamoyl)-2',3'-dihydro-1'H-spiro[piperidine-4,4'-quinoline]-1-yl)piperidine-1-carboxylate

HRID 2382991Notes

Reaction equation

HRID 2382991 reaction equation
[CH3:1][N:2]([CH3:26])[C:3]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]2([CH2:19][CH2:18][N:17]([CH:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[CH2:16][CH2:15]2)[CH2:7][CH2:6]1)=[O:4].C(N(CC)CC)C.[C:34](Cl)(=[O:40])[O:35][CH2:36][C:37]#[C:38][CH3:39]>C(#N)C.CO>[CH3:1][N:2]([CH3:26])[C:3]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]2([CH2:15][CH2:16][N:17]([CH:20]3[CH2:25][CH2:24][N:23]([C:34]([O:35][CH2:36][C:37]#[C:38][CH3:39])=[O:40])[CH2:22][CH2:21]3)[CH2:18][CH2:19]2)[CH2:7][CH2:6]1)=[O:4]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 41316692-Butyn-1-yl chloroformateHCID 24798103N,N-dimethyl-1-(piperidin-4-yl)-2',3'-dihydrospiro[piperidine-4,4'-quinoline]-1'-carboxamide

Product 1

HCID 24797832but-2-ynyl 4-(1'-(dimethylcarbamoyl)-2',3'-dihydro-1'H-spiro[piperidine-4,4'-quinoline]-1-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent2×

Procedure

N,N-dimethyl-1-(piperidin-4-yl)-2′,3′-dihydrospiro[piperidine-4,4′-quinoline]-1′-carboxamide 2ae (35.7 mg, 0.1 mmol) was dissolved in acetonitrile (1 mL) and triethylamine (100 uL) and treated with but-2-ynyl carbonochloridate (26.5 mg, 0.2 mmol). The reaction was stirred for 1 hour, then diluted with methanol (0.5 mL) and purified by HPLC (2-99% CH3CN gradient, 0.05% TFA) to yield compound no. 5. LC/MS (10-99% CH3CN/0.05% TFA gradient over 5 min): m/z 453.2, retention time 2.31 minutes. 1H-NMR (CDCl3, 400 MHz): δ 12.65 (br s, 1H), 7.69 (d, J=6.9 Hz, 1H), 7.13 (t, J=8.3 Hz, 1H), 7.02 (t, J=8.1 Hz, 1H), 6.83 (d, J=9.2 Hz, 1H), 4.66 (s, 2H), 4.38 (br s, 2H), 3.58 (m, 2H), 3.45 (m, 2H), 3.31 (m, 1H), 3.08 (m, 5H), 2.85 (s, 6H), 2.37 (m, 2H), 1.97 (m, 2H), 1.86 (t, J=2.3 Hz, 3H), 1.81 (m, 3H), 1.42 (t, J=7.3 Hz, 2H).

Workup

  1. custompurified by HPLC (2-99% CH3CN gradient, 0.05% TFA)
  2. customto yield compound no

Sources & evidence

ORD record
ord-cd2f2287493a4aa39b91fa1975defff2
Source dataset
uspto-grants-2012_09
Patent number
US08263605B2

Reaction notes

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