Diisopropylethylamine → (S)-1-(4-(2-fluoro-4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazin-1-yl) propan-2-ol

HRID 531702Notes

Reaction equation

HRID 531702 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:14]2[CH:15]=[C:16]3[C:22]([C:23]4[CH:24]=[N:25][N:26]([CH2:28][C:29]5[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=5)[CH:27]=4)=[CH:21][N:20]([S:36]([C:39]4[CH:45]=[CH:44][C:42]([CH3:43])=[CH:41][CH:40]=4)(=[O:38])=[O:37])[C:17]3=[N:18][CH:19]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.[CH3:46][C@H:47]1[CH2:49][O:48]1.CCN(C(C)C)C(C)C>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([C:14]2[CH:15]=[C:16]3[C:22]([C:23]4[CH:24]=[N:25][N:26]([CH2:28][C:29]5[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=5)[CH:27]=4)=[CH:21][N:20]([S:36]([C:39]4[CH:40]=[CH:41][C:42]([CH3:43])=[CH:44][CH:45]=4)(=[O:38])=[O:37])[C:17]3=[N:18][CH:19]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:9][CH2:10][N:11]([CH2:46][C@@H:47]([OH:48])[CH3:49])[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 146262(2S)-2-MethyloxiraneHCID 1185239985-(3-fluoro-4-(piperazin-1-yl)phenyl)-3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 90033580(S)-1-(4-(2-fluoro-4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazin-1-yl) propan-2-olYield 76.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Using similar reaction conditions as described in step-i of example-82A, 5-(3-fluoro-4-(piperazin-1-yl)phenyl)-3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (120 mg. 0.192 mmol) was alkylated using (S)-2-methyloxirane (14 mg, 0.23 mmol), DIPEA (50 mg, 0.384 mmol) and ethanol (5 mL) to get 100 mg (76.9% yield) of the titled compound. MS: m/z=683.2 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-d879a4b9ab004cfe9de8b7bc9001b21d
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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