1,2-Dichloroethane → HCID 59160537, compound

HRID 1958669Notes

Reaction equation

HRID 1958669 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]2[NH:13][C:14]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([CH3:33])[N:28]=3)=[C:15]([C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][CH:26]=3)[N:23]=[CH:22][CH:21]=[CH:20]4)[N:16]=2)=[CH:7][C:3]=1[C:4]([OH:6])=O.C1C=CC2N(O)N=NC=2C=1.[NH2:44][CH2:45][CH2:46][OH:47].C(Cl)CCl>CN(C1C=CN=CC=1)C.N1C=CC=CC=1.O>[F:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]2[NH:13][C:14]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([CH3:33])[N:28]=3)=[C:15]([C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][CH:26]=3)[N:23]=[CH:22][CH:21]=[CH:20]4)[N:16]=2)=[CH:7][C:3]=1[C:4]([NH:44][CH2:45][CH2:46][OH:47])=[O:6]

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 700EthanolamineHCID 757711-HydroxybenzotriazoleHCID 59160544HCID 59160544, compound

Product 1

HCID 59160537HCID 59160537, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A mixture of 2-fluoro-5-((5-(6-methylpyridin-2-yl)-4-(quinolin-6-yl)-1H-imidazol-2-yl)methyl)benzoic acid (Example 104) (50 mg, 0.114 mmol), HOBt (23 mg, 0.171 mmol), DMAP (3 mg, 0.023 mmol), and 2-aminoethanol in pyridine (1 mL) was added EDC (33 mg, 0.171 mmol) and the mixture was stirred at room temperature for 4 hours. The reaction mixture was poured into H2O and extracted with CH2Cl2 (5 mL, 3 times). The organic layer was dried over Na2SO4, filtered, and evaporated under reduced pressure. The residue was purified by MPLC (MeOH:CH2Cl2=1:100 (v/v) to 1:20 (v/v)) to afford the title compound (34.7 mg, 61%). (300 MHz, CDCl3) δ 2.37 (3H, s), 3.57 (2H, q), 3.79 (2H, t), 4.15 (2H, s), 6.91 (1H, dd), 6.96 (1H, d), 7.04-7.15 (1H, m), 7.20-7.30 (1H, m), 7.37-7.43 (2H, m), 7.80 (1H, dd), 7.85 (1H, dd), 8.04 (1H, d), 8.10 (1H, d), 8.14 (1H, dd), 8.90 (1H, dd), MS (ESI) m/z 482 (MH+).

Workup

  1. extractionextracted with CH2Cl2 (5 mL, 3 times)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by MPLC (MeOH:CH2Cl2=1:100 (v/v) to 1:20 (v/v))

Sources & evidence

ORD record
ord-e5b398e217394943bf9d17879728b14b
Source dataset
uspto-grants-2013_04
Patent number
US08410146B2

Reaction notes

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