1-Hydroxybenzotriazole → 2-cyclopropyl-1-(4-(4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazin-1-yl)ethanone

HRID 531735Notes

Reaction equation

HRID 531735 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:42]=[CH:43][CH:44]=1)[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH:25]=[CH:24][C:23]([N:26]5[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]5)=[CH:22][CH:21]=4)[CH:18]=3)[N:13]([S:32]([C:35]3[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=3)(=[O:34])=[O:33])[CH:12]=2)[CH:8]=[N:7]1.Cl.[CH:46]1([CH2:49][C:50](O)=[O:51])[CH2:48][CH2:47]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH:46]1([CH2:49][C:50]([N:29]2[CH2:28][CH2:27][N:26]([C:23]3[CH:24]=[CH:25][C:20]([C:17]4[CH:18]=[C:19]5[C:11]([C:9]6[CH:8]=[N:7][N:6]([CH2:5][C:4]7[CH:42]=[CH:43][CH:44]=[C:2]([F:1])[CH:3]=7)[CH:10]=6)=[CH:12][N:13]([S:32]([C:35]6[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=6)(=[O:33])=[O:34])[C:14]5=[N:15][CH:16]=4)=[CH:21][CH:22]=3)[CH2:31][CH2:30]2)=[O:51])[CH2:48][CH2:47]1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 676603122-Cyclopropylacetic acid hydrochlorideHCID 900312383-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(piperazin-1-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 900301172-cyclopropyl-1-(4-(4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazin-1-yl)ethanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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 (75 mg, 0.123 mmol) and 2-cyclopropylacetic acid hydrochloride (26 mg, 0.185 mmol) in DMF (2 mL) was added HATU (71 mg, 0.185 mmol), HOBt (25 mg, 0.185 mmol) and DIPEA (86 μL, 0.494 mmol) and stirred at RT overnight. Added ice water and extracted with 10% methanol in DCM. Organic layer was washed with brine solution, dried over sodium sulphate and distilled out the solvent to get 60 mg (70.58%) yield of the title compound. MS: m/z=689.2 (M+1).

Workup

  1. extractionAdded ice water and extracted with 10% methanol in DCM
  2. washOrganic layer was washed with brine solution
  3. dry with materialdried over sodium sulphate
  4. distillationdistilled out the solvent

Sources & evidence

ORD record
ord-42582faea0394ffab1f6fb6206137863
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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