Water → HCID 131732144, compound

HRID 1400079Notes

Reaction equation

HRID 1400079 reaction equation
[NH2:1][C@H:2]1[CH2:9][C@@:8]2([C:10]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:11])[C@H:4]([CH2:5][CH2:6][CH2:7]2)[CH2:3]1.Br[CH2:21][CH2:22][CH:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:24]Br.[CH:32](N(CC)C(C)C)(C)C.O>C(#N)C>[C:26]1([CH:23]2[CH2:24][CH2:32][N:1]([C@H:2]3[CH2:9][C@@:8]4([C:10]([O:12][CH2:13][C:14]5[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=5)=[O:11])[C@H:4]([CH2:5][CH2:6][CH2:7]4)[CH2:3]3)[CH2:21][CH2:22]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 562001HCID 562001, compoundHCID 131732142HCID 131732142, compound

Product 1

HCID 131732144HCID 131732144, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The mixture of Example 48D, (3-bromo-1-bromomethyl-propyl)-benzene (1.82 g, 5.9 mmol) and N,N-diisopropylethyl amine (2.1 g, 16.2 mmol) in acetonitrile (10 ml) was stirred at 120° C. in a microwave reactor for 2 hours. Water (15 mL) was added and extracted with ethyl acetate. The combined organics were dried and concentrated. The residue was purified by column chromatography (SiO2, petroleum ether: ethyl acetate from 50:1 to 10:1) to provide the title compound as an oil. 1H NMR (400 MHz, CDCl3) δ (ppm): 7.10-7.31 (m, 10H), 5.01-5.08 (s, 2H), 3.17 (d, 2H), 2.76 (q, 1H), 2.52-2.69 (m, 1H), 2.35-2.48 (m, 1H), 2.17-2.22 (m, 1H), 1.82-2.15 (m, 5H), 1.61-1.80 (m, 6H), 1.39-1.60 (m, 5H), 1.17-1.27 (m, 1H).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe combined organics were dried
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (SiO2, petroleum ether: ethyl acetate from 50:1 to 10:1)

Sources & evidence

ORD record
ord-fbba6f7313f442c7aaf73b945799bd7b
Source dataset
uspto-grants-2014_12
Patent number
US08906911B2

Reaction notes

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