Diisopropylethylamine → HCID 178441231, compound

HRID 406295Notes

Reaction equation

HRID 406295 reaction equation
[CH3:1][C:2]([C:5]1[C:10]([F:11])=[CH:9][C:8]([O:12][C@H:13]2[CH2:16][C@H:15]([NH2:17])[CH2:14]2)=[CH:7][C:6]=1[F:18])([CH3:4])[CH3:3].CCN(C(C)C)C(C)C.[N:28]1[CH:29]=[CH:30][N:31]2[CH:36]=[CH:35][CH:34]=[C:33]([CH:37]=O)[C:32]=12.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.O>[CH3:4][C:2]([C:5]1[C:6]([F:18])=[CH:7][C:8]([O:12][C@H:13]2[CH2:14][C@H:15]([NH:17][CH2:37][C:33]3[C:32]4[N:31]([CH:30]=[CH:29][N:28]=4)[CH:36]=[CH:35][CH:34]=3)[CH2:16]2)=[CH:9][C:10]=1[F:11])([CH3:1])[CH3:3]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 10997174Imidazo(1,2-a)pyridine-8-carbaldehydeHCID 178441228HCID 178441228, compound

Product 1

HCID 178441231HCID 178441231, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A suspension of trans-3-{[4-(1,1-dimethylethyl)-3,5-difluorophenyl]oxy}cyclobutanamine (73 mg, 0.286 mmol) in anhydrous DCM (3 mL) was treated with DIPEA (0.06 mL, 0.343 mmol). A solution of imidazo[1,2-a]pyridine-8-carbaldehyde (41.8 mg, 0.286 mmol) in anhydrous DCM (3 mL) was added and the reaction was stirred at room temperature for 15 min. Sodium triacetoxyborohydride (121 mg, 0.572 mmol) was added portionwise and the reaction was stirred at room temperature under nitrogen overnight. Water (10 mL) was added and the phases were separated. The organic layer was concentrated and the residue was purified by MDAP to give the title compound (79.4 mg).

Workup

  1. stirringthe reaction was stirred at room temperature under nitrogen overnight
  2. customthe phases were separated
  3. concentrationThe organic layer was concentrated
  4. customthe residue was purified by MDAP

Sources & evidence

ORD record
ord-28dd76bafc1648c18b294913da40328c
Source dataset
uspto-grants-2014_06
Patent number
US08754101B2

Reaction notes

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