Ammonia → HCID 86610955, compound

HRID 2250386Notes

Reaction equation

HRID 2250386 reaction equation
C[C:2]1[C:3]([NH:13][C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:10](O)=[O:11])[NH:4][CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[H-].C([Al+]CC(C)C)C(C)C.C(OCC)C.N>C1(C)C=CC=CC=1.C(O)(=O)C>[CH3:9][O:8][C:7]1[CH:6]=[CH:5][NH:4][C:3]([NH:13][C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([CH:10]=[O:11])[CH:2]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 3283Diethyl EtherHCID 21225700DiisobutylaluminumhydrideHCID 86610956HCID 86610956, compound

Product 1

HCID 86610955HCID 86610955, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
-70 °C

Procedure

1.19 g of methyl 4-methoxy-2-(trityl-amino)-picolinic acid (compound B12) are dissolved in 41 ml of toluene. Subsequently, the solution is cooled to −70° C. and 3.36 ml of diisobutylaluminium hydride in toluene (strength 1.5 M) are added dropwise. After 30 min, 6.0 ml of diethyl ether and 3.5 ml of aqueous acetic acid (20% strength) are added. After further 30 min, the mixture is allowed to warm up to room temperature. Subsequently, 34 ml of aqueous ammonia (25% strength) is added and the mixture is filtered through a celite pad. The filter cake is rinsed with 50 ml of toluene. The filtrate is extracted three times each with 70 ml of sat sodium chloride solution. The organic layer is dried using sodium sulphate, filtered with suction and concentrated in vacuum. The crude product (1.36 g) is purified by chromatography (eluent: toluene/ethyl acetate 10:1) to yield 898 mg of the title compound as an amorphous solid. M.p. 172° C. TSP-MS: 395.2 [MH+]. TLC: Rf=0.40 (toluene/ethyl acetate 10:1).

Workup

  1. waitAfter further 30 min
  2. temperatureto warm up to room temperature
  3. filtrationthe mixture is filtered through a celite pad
  4. washThe filter cake is rinsed with 50 ml of toluene
  5. extractionThe filtrate is extracted three times each with 70 ml of sat sodium chloride solution
  6. customThe organic layer is dried
  7. filtrationfiltered with suction
  8. concentrationconcentrated in vacuum
  9. customThe crude product (1.36 g) is purified by chromatography (eluent: toluene/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-bf8e48fe959a41ba8f19c9bab053482f
Source dataset
uspto-grants-2008_01
Patent number
US07317021B2

Reaction notes

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