Urea → HCID 178471765, compound

HRID 220154Notes

Reaction equation

HRID 220154 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C@H:11]2[CH2:16][CH2:15][C@H:14]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)=O.[NH2:23][C:24]([NH2:26])=[O:25].CN(C)[CH:29]=[O:30]>>[CH:29]([NH:23][C:24]1[O:25][CH:2]=[C:3]([C:5]2[CH:10]=[CH:9][C:8]([C@H:11]3[CH2:16][CH2:15][C@H:14]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:13][CH2:12]3)=[CH:7][CH:6]=2)[N:26]=1)=[O:30]

Participants

4

Reactant 3

HCID 1176UreaHCID 6228DimethylformamideHCID 178471769HCID 178471769, compound

Product 1

HCID 178471765HCID 178471765, compound

Conditions

Temperature
92.5 °C

Procedure

A mixture of the product from Example 48A (100 mg, 0.27 mmol) and urea (33 mg, 0.54 mmol) in N,N-dimethylformamide (5 mL) was heated at 90-95° C. under N2 for 2 hours. The mixture was concentrated, and purified on a RP-HPLC to provide the title product. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.13 (m, 2H), 1.19 (t, J=7.05 Hz, 3H), 1.48 (m, 2H), 1.69-1.85 (m, 5H), 2.22 (d, J=6.75 Hz, 2H), 2.47 (m, 1H), 4.07 (q, J=7.05 Hz, 3H), 4.14 (m, 1H), 7.28 (d, J=8.29 Hz, 2H), 7.63 (d, J=8.29 Hz, 2H), 8.29 (s, 1H), 8.95 (br s, 1H), 11.50 (br s, 1H); MS (ESI) m/z 356.9 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified on a RP-HPLC

Sources & evidence

ORD record
ord-d136f6616fda4715a4f337299f297e02
Source dataset
uspto-grants-2012_06
Patent number
US08202878B2

Reaction notes

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