Diisopropylethylamine → HCID 89738582, compound

HRID 592056Notes

Reaction equation

HRID 592056 reaction equation
[NH2:1][C@@H:2]1[C@@H:7]2[O:8][C@@H:4]([CH2:5][CH2:6]2)[C@@H:3]1[C:9]([NH2:11])=[O:10].Cl[C:13]1[C:18]([Cl:19])=[CH:17][N:16]=[C:15]([NH2:20])[C:14]=1[N+:21]([O-:23])=[O:22].CCN(C(C)C)C(C)C>CC(O)C>[NH2:20][C:15]1[C:14]([N+:21]([O-:23])=[O:22])=[C:13]([NH:1][C@@H:2]2[C@@H:7]3[O:8][C@@H:4]([CH2:5][CH2:6]3)[C@@H:3]2[C:9]([NH2:11])=[O:10])[C:18]([Cl:19])=[CH:17][N:16]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 468676602-Amino-4,5-dichloro-3-nitropyridineHCID 89738583HCID 89738583, compound

Product 1

HCID 89738582HCID 89738582, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

(1S,2R,3S,4R)-3-amino-7-oxabicyclo[2.2.1]heptane-2-carboxamide (15) (170 mg, 0.67 mmol), 4,5-dichloro-3-nitropyridin-2-amine (127 mg, 0.6 mmol), DIPEA (5.5 eq) were taken in IPA and heated at 60° C. for 15 h when a yellow precipitate appeared. The precipitate was filtered, washed well with IPA and dried to afford the desired product, (198 mg, 34%).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed well with IPA
  3. customdried

Sources & evidence

ORD record
ord-eb295ac296f1431393cf5b542760d782
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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