Benzyl Bromide → HCID 66808377, compound

HRID 607265Notes

Reaction equation

HRID 607265 reaction equation
C(OC(=O)[N:7]([C:23]1[C:32]2[C:27](=[N:28][C:29]([S:33][CH2:34][CH3:35])=[N:30][CH:31]=2)[N:26]=[CH:25][N:24]=1)[C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=1[S:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)(C)(C)C.[CH2:37](Br)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.BrCC#N>>[CH2:37]([O:22][C:19]1[CH:20]=[CH:21][C:16]([S:15][C:9]2[CH:10]=[CH:11][C:12]([CH3:14])=[CH:13][C:8]=2[NH:7][C:23]2[C:32]3[C:27](=[N:28][C:29]([S:33][CH2:34][CH3:35])=[N:30][CH:31]=3)[N:26]=[CH:25][N:24]=2)=[CH:17][CH:18]=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

4

Reactant 3

HCID 7498Benzyl Bromide2×HCID 11534BromoacetonitrileHCID 66808367HCID 66808367, compound

Product 1

HCID 66808377HCID 66808377, compoundYield 29%

Procedure

The product from Example 164 was reacted with benzyl bromide according to the procedure from Example 165 substituting benzyl bromide for bromo-acetonitrile to provide the crude product which was purified by silica gel chromatography using 98/2 dichloromethane/methanol as eluent to provide the title compound (15 mg, 29%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.20 (t, J=7.35 Hz, 3H), 2.27 (s, 3H), 3.08 (q, J=7.35 Hz, 2H), 5.44 (s, 2H), 6.74 (d, J=8.46 Hz, 2H), 6.95 (m, 3H), 7.20 (d, J=8.46 Hz, 2H), 7.35 (m, 5H), 8.77 (s, 1H), 9.42 (s, 1H), 9.81 (s, 1H); MS (ESI+) m/z 512 (M+H)+.

Workup

  1. customto provide the crude product which
  2. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-b772ea7cc95f41d3a6be734f375deaac
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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