Dichloromethane → HCID 73056875, compound

HRID 1846212Notes

Reaction equation

HRID 1846212 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2([NH2:19])[C:18]3[N:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C(Cl)Cl.CCN(C(C)C)C(C)C.[C:34](Cl)(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>O>[F:21][C:2]([F:1])([F:20])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2([NH:19][C:34](=[O:41])[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:18]3[N:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 89964488HCID 89964488, compound

Product 1

HCID 73056875HCID 73056875, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 0° C. solution of 8-(4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydroquinolin-8-amine (62 mg, 0.136 mmol) and DCM (1 mL) was added DIEA (0.035 mL, 0.201 mmol) and then benzoyl chloride (0.0175 mL, 0.151 mmol) dropwise. After 1 h, the reaction was poured into water and the aqueous layer back extracted with DCM (5 mL). The combined DCM layers were concentrated in vacuo and adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep® pre-packed silica gel column (12 g), eluting with 0-30% EtOAc in hexane, to provide the title compound as a white solid. MS (ESI, positive ion) m/z: 397.0 (MH+). 1H NMR (300MHz, CDCl3) δ: 8.46-8.63 (m, 2H), 7.74-7.88 (m, 2H), 7.33-7.66 (m, 8H), 7.24-7.28 (m, 1H), 3.55 (dt, J=14.0, 4.2 Hz, 1H), 2.89 (dd, J=9.6, 6.8 Hz, 1H), 2.54-2.82 (m, 2H), 1.86-2.01 (m, 1H), 1.65-1.83 (m, 1H).

Workup

  1. extractionthe aqueous layer back extracted with DCM (5 mL)
  2. concentrationThe combined DCM layers were concentrated in vacuo
  3. customchromatographed through a Redi-Sep® pre-packed silica gel column (12 g)
  4. washeluting with 0-30% EtOAc in hexane

Sources & evidence

ORD record
ord-1f58e9327cdf4aa68fb7e430e8dc49c8
Source dataset
uspto-grants-2015_02
Patent number
US08952009B2

Reaction notes

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