Diisopropylethylamine → HCID 90030672, compound

HRID 531706Notes

Reaction equation

HRID 531706 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([CH:44]=[CH:45][CH:46]=1)[CH2:6][N:7]1[CH:11]=[C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][C:24]([N:27]5[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]5)=[C:23]([CH3:33])[CH:22]=4)[CH:19]=3)[N:14]([S:34]([C:37]3[CH:43]=[CH:42][C:40]([CH3:41])=[CH:39][CH:38]=3)(=[O:36])=[O:35])[CH:13]=2)[CH:9]=[N:8]1.[CH3:47][C@H:48]1[CH2:50][O:49]1.CCN(C(C)C)C(C)C>C(O)C>[F:2][C:3]1[CH:4]=[C:5]([CH:44]=[CH:45][CH:46]=1)[CH2:6][N:7]1[CH:11]=[C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][C:24]([N:27]5[CH2:28][CH2:29][N:30]([CH2:47][C@@H:48]([OH:49])[CH3:50])[CH2:31][CH2:32]5)=[C:23]([CH3:33])[CH:22]=4)[CH:19]=3)[N:14]([S:34]([C:37]3[CH:38]=[CH:39][C:40]([CH3:41])=[CH:42][CH:43]=3)(=[O:35])=[O:36])[CH:13]=2)[CH:9]=[N:8]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 146262(2S)-2-MethyloxiraneHCID 90031113HCID 90031113, compound

Product 1

HCID 90030672HCID 90030672, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Using similar reaction conditions as described in step-i of example-82A, 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(3-methyl-4-(piperazin-1-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine hydrochloride (172 mg. 0.277 mmol) was alkylated using (S)-2-methyloxirane (24 mg, 0.416 mmol), DIPEA (54 mg, 0.416 mmol) and ethanol (4 mL) to get 183 mg (97.3% yield) of the titled compound. MS: m/z=679.3 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-655ca994359543fbb4a9e368b156d264
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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