Triethylamine → HCID 71547492, compound

HRID 1184549Notes

Reaction equation

HRID 1184549 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[CH:5][C:6]([NH:9][C@@H:10]2[CH2:18][N:13]3[CH2:14][CH2:15][NH:16][CH2:17][C@@H:12]3[CH2:11]2)=[N:7][CH:8]=1.C(N(CC)CC)C.[CH2:28]([CH:30]([CH2:34][CH3:35])[C:31](Cl)=[O:32])[CH3:29]>ClCCl>[CH2:28]([CH:30]([CH2:34][CH3:35])[C:31]([N:16]1[CH2:15][CH2:14][N:13]2[CH2:18][C@@H:10]([NH:9][C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:19])[F:20])=[CH:8][N:7]=3)[CH2:11][C@H:12]2[CH2:17]1)=[O:32])[CH3:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 759542-Ethylbutyryl chlorideHCID 71547491HCID 71547491, compound

Product 1

HCID 71547492HCID 71547492, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Example 20 (286 mg, 1 mmol) and triethylamine (202 mg, 2 mmol) in dichloromethane (5 mL) was added 2-ethylbutanoyl chloride (141 mg, 1.05 mmol) in dichloromethane (1 mL). The mixture was stirred room temperature for 2 hours, and then concentrated. The residue was purified by chromatography on silica gel (ethyl acetate/methanol=10:1) to give the title compound. 1H NMR(400 MHz, DMSO-d6) δ ppm 0.80 (m, 6H), 1.35 (m, 3H), 1.50 (m, 3H), 1.80-2.00 (m, 2H), 2.35 (m, 3H), 2.60-3.07 (m, 3H), 4.02-4.10 (m, 1H), 4.33 (m, 1H), 4.48-4.60 (m, 1H), 6.60 (d, 1H, J=7 Hz), 7.56 (m, 1H), 7.60 (d, 1H, J=7 Hz), 8.28 (s, 1H); MS (ESI) m/z 385 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by chromatography on silica gel (ethyl acetate/methanol=10:1)

Sources & evidence

ORD record
ord-71c26dc4e02342589a80a1ec0c1adbcf
Source dataset
uspto-grants-2014_03
Patent number
US08669255B2

Reaction notes

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