Ammonia → 4-(4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) piperazine-1-carboxamide

HRID 531686Notes

Reaction equation

HRID 531686 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([CH:43]=[CH:44][CH:45]=1)[CH2:6][N:7]1[CH:11]=[C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][C:24]([N:27]5[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]5)=[CH:23][CH:22]=4)[CH:19]=3)[N:14]([S:33]([C:36]3[CH:42]=[CH:41][C:39]([CH3:40])=[CH:38][CH:37]=3)(=[O:35])=[O:34])[CH:13]=2)[CH:9]=[N:8]1.ClC(Cl)(O[C:50](=[O:56])OC(Cl)(Cl)Cl)Cl.[NH3:58]>C(Cl)(Cl)Cl.C1COCC1.O>[F:2][C:3]1[CH:4]=[C:5]([CH:43]=[CH:44][CH:45]=1)[CH2:6][N:7]1[CH:11]=[C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][C:24]([N:27]5[CH2:28][CH2:29][N:30]([C:50]([NH2:58])=[O:56])[CH2:31][CH2:32]5)=[CH:23][CH:22]=4)[CH:19]=3)[N:14]([S:33]([C:36]3[CH:42]=[CH:41][C:39]([CH3:40])=[CH:38][CH:37]=3)(=[O:34])=[O:35])[CH:13]=2)[CH:9]=[N:8]1

Participants

7

Reactant 3

HCID 222AmmoniaHCID 94429TriphosgeneHCID 900315073-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(piperazin-1-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridinehydrochloride

Product 1

HCID 1185240084-(4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) piperazine-1-carboxamideYield 26.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(piperazin-1-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine hydrochloride (step 1 example 103) (150 mg. 0.233 mmol) in chloroform (10 mL) triethyl amine (0.16 mL, 1.165 mmol) was added at 0° C. drop wise. This solution was added to a solution of triphosgene (59 mg, 0.233 mmol) in chloroform (10 mL) and stirred at RT for 30 minutes. Ammonia in THF was added to this solution drop wise and stirred at RT overnight. This was diluted with water and extracted in chloroform and distilled out the solvent to afford the 40 mg (26.4% yield) of the titled compound after purification with preparative TLC (silicagel-1000 micron) using 3% methanol in DCM as eluent. MS: m/z=649.7 (M+1).

Workup

  1. stirringstirred at RT overnight
  2. extractionextracted in chloroform
  3. distillationdistilled out the solvent

Sources & evidence

ORD record
ord-dd8a6a6ec3c441bbb615e77318c271ca
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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