Triethylamine → HCID 58451298, compound

HRID 2366800Notes

Reaction equation

HRID 2366800 reaction equation
[C:1](=[O:12])(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl.[NH2:13][C:14]1[CH:15]=[C:16]([CH:33]=[CH:34][C:35]=1[F:36])[O:17][C:18]1[N:23]=[C:22]2[S:24][C:25]([NH:27][C:28]([CH:30]3[CH2:32][CH2:31]3)=[O:29])=[N:26][C:21]2=[CH:20][CH:19]=1.C(N(CC)CC)C.[F:44][C:45]([F:55])([F:54])[C:46]1[CH:51]=[CH:50][C:49]([CH2:52][NH2:53])=[CH:48][CH:47]=1>O1CCCC1.C(OCC)(=O)C>[F:36][C:35]1[CH:34]=[CH:33][C:16]([O:17][C:18]2[N:23]=[C:22]3[S:24][C:25]([NH:27][C:28]([CH:30]4[CH2:32][CH2:31]4)=[O:29])=[N:26][C:21]3=[CH:20][CH:19]=2)=[CH:15][C:14]=1[NH:13][C:1](=[O:12])[NH:53][CH2:52][C:49]1[CH:48]=[CH:47][C:46]([C:45]([F:44])([F:54])[F:55])=[CH:51][CH:50]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 768044-(Trifluoromethyl)benzylamineHCID 94429TriphosgeneHCID 86646022N-[5-(3-amino-4-fluorophenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]cyclopropanecarboxamide

Product 1

HCID 58451298HCID 58451298, compoundYield 116.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of bis(trichloromethyl) carbonate (30 mg, 0.102 mmol) in tetrahydrofuran (2 mL) was added dropwise a suspension of N-[5-(3-amino-4-fluorophenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]cyclopropanecarboxamide (100 mg, 0.290 mmol) produced in Example 16(vi) and triethylamine (80 μL, 0.580 mmol) in tetrahydrofuran (2 mL) at 0° C., and the mixture was stirred at 0° C. for 30 min. 1-[4-(Trifluoromethyl)phenyl]methanamine (50 μL, 0.348 mmol) was added to the reaction mixture, and the mixture was stirred at room temperature for 1.5 hr. The reaction mixture was diluted with ethyl acetate (20 mL), and washed successively with aqueous sodium hydrogen carbonate solution (15 mL) and saturated brine (5 mL). The solid precipitated in the organic layer was collected by filtration to give the title compound (65 mg, 41%) as a white solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 1.5 hr
  2. washwashed successively with aqueous sodium hydrogen carbonate solution (15 mL) and saturated brine (5 mL)
  3. customThe solid precipitated in the organic layer
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-4b0d28ca504b47a28467709e1bbb2533
Source dataset
uspto-grants-2014_04
Patent number
US08697874B2

Reaction notes

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