Ammonia → HCID 21949757, compound

HRID 558280Notes

Reaction equation

HRID 558280 reaction equation
Br[CH2:2][C:3]1[N:7]([CH2:8][CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[N:6]=[C:5]([CH2:18][CH3:19])[C:4]=1[O:20][C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=1.N.C([N:33](C(C)C)CC)(C)C>C(O)(C)C>[NH2:33][CH2:2][C:3]1[N:7]([CH2:8][CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[N:6]=[C:5]([CH2:18][CH3:19])[C:4]=1[O:20][C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 21949785HCID 21949785, compound

Product 1

HCID 21949757HCID 21949757, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The bromide of Example 137 (444 mg, 0.900 mmol) was added to a saturated solution of ammonia in isopropanol (25 ml) and diisopropylethylamine (173 μl, 1.00 mmol) at room temperature. The reaction was stirred for 5 hours and then concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (95:5, by volume) to provide the title compound (359 mg) as a white solid, m.p. 112-114° C.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (95:5, by volume)

Sources & evidence

ORD record
ord-6447527333f54b1aa45ea31bb74a3203
Source dataset
uspto-grants-2011_11
Patent number
US08063044B2

Reaction notes

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