Diisopropylethylamine → HCID 118523908, compound

HRID 531727Notes

Reaction equation

HRID 531727 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:5]=[CH:4][C:3]=1[C:14]1[CH:15]=[C:16]2[C:22]([C:23]3[CH:24]=[N:25][N:26]([CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=4)[CH:27]=3)=[CH:21][N:20]([S:36]([C:39]3[CH:45]=[CH:44][C:42]([CH3:43])=[CH:41][CH:40]=3)(=[O:38])=[O:37])[C:17]2=[N:18][CH:19]=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:7]=[C:6]([N:8]2[CH2:9][CH2:10][N:11]([CH2:46][C@@H:47]([OH:48])[CH3:49])[CH2:12][CH2:13]2)[CH:5]=[CH:4][C:3]=1[C:14]1[CH:15]=[C:16]2[C:22]([C:23]3[CH:24]=[N:25][N:26]([CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=4)[CH:27]=3)=[CH:21][N:20]([S:36]([C:39]3[CH:40]=[CH:41][C:42]([CH3:43])=[CH:44][CH:45]=3)(=[O:38])=[O:37])[C:17]2=[N:18][CH:19]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 146262(2S)-2-MethyloxiraneHCID 118524009HCID 118524009, compound

Product 1

HCID 118523908HCID 118523908, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Using similar reaction conditions as described in step-i of example-82A, 5-(2-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 (17 mg, 0.288 mmol), DIPEA (75 mg, 0.576 mmol) and ethanol (3 mL) to get 100 mg (76.3%) of the titled compound. MS: m/z=683.2 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-bc125196c3d44b8cba2733c2e76ffb7b
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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