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

HRID 531811Notes

Reaction equation

HRID 531811 reaction equation
COC1C=CC(B2[O:13][C:12](C)(C)[C:11]([CH3:17])([CH3:16])O2)=CC=1CS(N)(=O)=O.[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.C1(C(Cl)=O)CC1.C(N(CC)CC)C>C(Cl)Cl>[CH:11]1([C:12]([N:51]2[CH2:52][CH2:53][N:48]([C:45]3[CH:46]=[CH:47][C:42]([C:39]4[CH:40]=[C:41]5[C:33]([C:31]6[CH:30]=[N:29][N:28]([CH2:27][C:26]7[CH:64]=[CH:65][CH:66]=[C:24]([F:23])[CH:25]=7)[CH:32]=6)=[CH:34][N:35]([S:54]([C:57]6[CH:63]=[CH:62][C:60]([CH3:61])=[CH:59][CH:58]=6)(=[O:56])=[O:55])[C:36]5=[N:37][CH:38]=4)=[CH:43][N:44]=3)[CH2:49][CH2:50]2)=[O:13])[CH2:17][CH2:16]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl 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 90031347cyclopropyl(4-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl)methanoneYield 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 acylated with cyclopropane carbonyl chloride (22 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=676.2 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-1802753e95994ee1a432ce697abadcc7
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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