Diisopropylethylamine → HCID 118318877, compound

HRID 921230Notes

Reaction equation

HRID 921230 reaction equation
[CH2:1]([O:4][C:5]1([CH3:34])[CH2:10][CH2:9][N:8]([C:11]2[N:16]3[N:17]=[C:18]([CH2:20]I)[CH:19]=[C:15]3[N:14]=[C:13]([CH3:22])[C:12]=2[C@H:23]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:7][CH2:6]1)[CH:2]=[CH2:3].[CH3:35][C:36]1[CH:46]=[CH:45][C:39]([CH2:40][NH:41][CH:42]2[CH2:44][CH2:43]2)=[C:38]([O:47][C@H:48]([CH2:50][CH:51]=[CH2:52])[CH3:49])[CH:37]=1.CCN(C(C)C)C(C)C>C(#N)C>[CH2:1]([O:4][C:5]1([CH3:34])[CH2:10][CH2:9][N:8]([C:11]2[N:16]3[N:17]=[C:18]([CH2:20][N:41]([CH:42]4[CH2:44][CH2:43]4)[CH2:40][C:39]4[CH:45]=[CH:46][C:36]([CH3:35])=[CH:37][C:38]=4[O:47][C@H:48]([CH2:50][CH:51]=[CH2:52])[CH3:49])[CH:19]=[C:15]3[N:14]=[C:13]([CH3:22])[C:12]=2[C@H:23]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:7][CH2:6]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 118307103HCID 118307103, compoundHCID 118318796(S)-ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(iodomethyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate

Product 1

HCID 118318877HCID 118318877, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of (S)-ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(iodomethyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (95 mg, 0.163 mmol) in acetonitrile (3 mL) at 0° C. was added (S)—N-(4-Methyl-2-(pent-4-en-2-yloxy)benzyl)cyclopropanamine (40 mg, 0.163 mmol) and Hunig's Base (0.028 mL, 0.163 mmol). It was stirred at 0° C. for 2 h and then quenched with water, extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated. The residue was then purify by 20% EtOAc/hexane to obtain (S)-ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-((cyclopropyl(4-methyl-2-((S)-pent-4-en-2-yloxy)benzyl)amino)methyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (90 mg, 0.128 mmol, 79% yield) as an oil. LCMS (M+1)=702.5.

Workup

  1. customquenched with water
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was then purify by 20% EtOAc/hexane

Sources & evidence

ORD record
ord-af3770c5d5214b49b8ee5eb474097035
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

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