Hydrochloric Acid → 6-[4-(2-Trifluoromethylphenylamino)piperidin-1-YL]pyridazine-3-carboxylic acid (2-cyclopropylethyl)amide hydrochloride

HRID 552148Notes

Reaction equation

HRID 552148 reaction equation
[CH:1]1([CH2:4][CH2:5][NH:6][C:7]([C:9]2[N:10]=[N:11][C:12]([N:15]3[CH2:20][CH2:19][CH:18]([NH:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[C:28]([F:31])([F:30])[F:29])[CH2:17][CH2:16]3)=[CH:13][CH:14]=2)=[O:8])[CH2:3][CH2:2]1.[ClH:32].CCOCC>ClCCl>[ClH:32].[CH:1]1([CH2:4][CH2:5][NH:6][C:7]([C:9]2[N:10]=[N:11][C:12]([N:15]3[CH2:20][CH2:19][CH:18]([NH:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[C:28]([F:29])([F:30])[F:31])[CH2:17][CH2:16]3)=[CH:13][CH:14]=2)=[O:8])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 11561097HCID 11561097, compound

Product 1

HCID 866171226-[4-(2-Trifluoromethylphenylamino)piperidin-1-YL]pyridazine-3-carboxylic acid (2-cyclopropylethyl)amide hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-[4-(2-Trifluoromethylphenylamino)piperidin-1-yl]pyridazine-3-carboxylic acid (2-cyclopropylethyl)amide was dissolved in dichloromethane (3 mL). Hydrochloric acid in ether (2 M, 0.18 mL, 0.36 mmol) was added to the solution. The mixture was kept at ambient temperature for 2 hours. The white precipitate obtained was collected by filtration and washed with ether and dried in vacuo to afford the title compound as a white solid (0.193 g). m.p. 158-163° C. 1H NMR (300 MHz, DMSO-d6) δ 6.7 2 (d, J=9.9 Hz, 1H), 6.53 (d, J=9.9 Hz, 1H), 5.86-5.82 (m, 2H), 5.43 (d, J=8.7 Hz, 1H), 5.18 (t, J=7.5 Hz, 1H), 2.73 (d, J=13.8 Hz, 2H), 2.42-2.35 (m, 1H), 2.07-1.89 (m, 4H), 0.74-0.70 (m, 2H), 0.21-0.17 (m, 2H), 0.01-−0.03 (m, 2H), −0.05-−0.10 (m, 2H), −0.77-−0.80 (m, 1H), −1.05-−1.18 (m, 2H), −1.42-−1.54 (m, 2H). 13C NMR (75 MHz, DMSO-d6) δ 162.1, 153.9, 145.6, 145.1, 134.5, 132.5, 127.7, 124.5, 117.6, 114.3, 49.5, 41.0, 35.4, 32.0, 9.4, 4.6. MS (ES+) m/z 434.3 (M+1-HCl).

Workup

  1. customThe white precipitate obtained
  2. filtrationwas collected by filtration
  3. washwashed with ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-4bd11c71cbcc438d80c16d9eeaf76f46
Source dataset
uspto-grants-2011_05
Patent number
US07951805B2

Reaction notes

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