Triethylamine → 5-(6-(4-(ethylsulfonyl)piperazin-1-yl)pyridin-3-yl)-3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

HRID 531809Notes

Reaction equation

HRID 531809 reaction equation
COC1C=CC(B2OC(C)(C)C(C)(C)O2)=C[C:4]=1[CH2:18][S:19](N)(=[O:21])=[O:20].[F:23][C:24]1[CH:25]=[C:26]([CH:64]=[CH:65][CH:66]=1)[CH2:27][N:28]1[CH:32]=[C:31]([C:33]2[C:41]3[C:36](=[N:37][CH:38]=[C:39]([C:42]4[CH:43]=[N:44][C:45]([N:48]5[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]5)=[CH:46][CH:47]=4)[CH:40]=3)[N:35]([S:54]([C:57]3[CH:63]=[CH:62][C:60]([CH3:61])=[CH:59][CH:58]=3)(=[O:56])=[O:55])[CH:34]=2)[CH:30]=[N:29]1.FC1C=C(C=CC=1)CN1C=C(C2C3C(=NC=C(C4C=NC(N5CCN(C)CC5)=CC=4)C=3)NC=2)C=N1.C(S(Cl)(=O)=O)C.C(N(CC)CC)C>C(Cl)Cl>[CH2:18]([S:19]([N:51]1[CH2:52][CH2:53][N:48]([C:45]2[N:44]=[CH:43][C:42]([C:39]3[CH:40]=[C:41]4[C:33]([C:31]5[CH:30]=[N:29][N:28]([CH2:27][C:26]6[CH:64]=[CH:65][CH:66]=[C:24]([F:23])[CH:25]=6)[CH:32]=5)=[CH:34][N:35]([S:54]([C:57]5[CH:63]=[CH:62][C:60]([CH3:61])=[CH:59][CH:58]=5)(=[O:56])=[O:55])[C:36]4=[N:37][CH:38]=3)=[CH:47][CH:46]=2)[CH2:49][CH2:50]1)(=[O:21])=[O:20])[CH3:4]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 900303003-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 900309313-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridineHCID 1317356682-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl methane sulfonamide

Product 1

HCID 1185240445-(6-(4-(ethylsulfonyl)piperazin-1-yl)pyridin-3-yl)-3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using similar reaction conditions as described in step i of intermediate 17, 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (step 1 compound of example 137) (80 mg, 0.13 mmol) was alkylated with ethanesulfonyl chloride (25 mg, 0.196 mmol) using triethylamine (40 mg, 0.39 mmol) in DCM (3 mL) to afford 100 mg (100% yield) of the titled compound. MS: m/z=700.2 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-70f5fee1d6cc4fef8fd78804f6de5a9e
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

Loading…