Triethylamine → HCID 46832654, compound

HRID 1882150Notes

Reaction equation

HRID 1882150 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=2/[CH:14]=[CH:15]/[C:16]2[N:17]=[C:18]3[N:22]([C:23]=2[C:24](O)=[O:25])[CH:21]=[CH:20][S:19]3)[CH2:3][CH2:2]1.[F:27][C:28]([F:42])([F:41])[C:29]1[CH:30]=[CH:31][C:32]([N:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)=[N:33][CH:34]=1.C(N(CC)CC)C>ClCCl>[CH:1]1([CH2:4][O:5][C:6]2[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=2/[CH:14]=[CH:15]/[C:16]2[N:17]=[C:18]3[N:22]([C:23]=2[C:24]([N:38]2[CH2:39][CH2:40][N:35]([C:32]4[CH:31]=[CH:30][C:29]([C:28]([F:42])([F:27])[F:41])=[CH:34][N:33]=4)[CH2:36][CH2:37]2)=[O:25])[CH:21]=[CH:20][S:19]3)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6676181-(5-Trifluoromethyl-pyridin-2-yl)-piperazineHCID 593698916-{(E)-2-[2-(Cyclopropylmethoxy)-3-methoxyphenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylic acid

Product 1

HCID 46832654HCID 46832654, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the general procedure (Method A) by coupling Intermediate 1 (50 mg, 0.134 mmol) with 1-[5-(trifluoromethyl)pyridin-2-yl]piperazine in the presence of triethylamine (34 mg, 0.337 mmol) in dichloromethane (5 mL) gave 46 mg of the product as an off-white solid; 1H NMR (300 MHz, CDCl3) δ 0.25-0.29 (m, 2H), 0.52-0.58 (m, 2H), 1.25-1.28 (m, 1H), 3.72-3.74 (m, 4H), 3.78-3.82 (m, 6H), 3.83 (s, 3H), 6.61 (d, J=9.0 Hz, 1H), 6.79-6.82 (m, 1H), 6.87-6.88 (m, 1H), 7.00 (t, J=7.8 Hz, 1H), 7.09-7.12 (m, 1H), 7.19-7.22 (m, 1H), 7.61-7.63 (m, 1H), 7.74 (d, J=3.9 Hz, 1H), 7.80 (d, J=15.9 Hz, 1H), 8.36 (br s, 1H); ESI-MS (m/z) 584.35 (MH)+.

Sources & evidence

ORD record
ord-7a653ee032fd4309be36fb1832b8bb02
Source dataset
uspto-grants-2012_11
Patent number
US08318928B2

Reaction notes

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