Diisobutylamine → HCID 57713867, compound

HRID 417838Notes

Reaction equation

HRID 417838 reaction equation
[Cl:1][C:2]1[C:3]2[C:17]([C:18]#[C:19][CH2:20]O)=[CH:16][N:15]([CH2:22][C:23]3[C:28]([CH3:29])=[C:27]([O:30][CH3:31])[C:26]([CH3:32])=[CH:25][N:24]=3)[C:4]=2[N:5]=[C:6]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[N:7]=1.CS(Cl)(=O)=O.S([O-])(=O)(=O)C.[CH2:43]([NH:47][CH2:48][CH:49]([CH3:51])[CH3:50])[CH:44]([CH3:46])[CH3:45]>C(Cl)Cl.CCN(CC)CC>[Cl:1][C:2]1[C:3]2[C:17]([C:18]#[C:19][CH2:20][N:47]([CH2:48][CH:49]([CH3:51])[CH3:50])[CH2:43][CH:44]([CH3:46])[CH3:45])=[CH:16][N:15]([CH2:22][C:23]3[C:28]([CH3:29])=[C:27]([O:30][CH3:31])[C:26]([CH3:32])=[CH:25][N:24]=3)[C:4]=2[N:5]=[C:6]([NH:8][C:9](=[O:14])[C:10]([CH3:11])([CH3:12])[CH3:13])[N:7]=1

Participants

7

Reactant 4

HCID 8085DiisobutylamineHCID 31297Methanesulfonyl chlorideHCID 85257MethanesulfonateHCID 57713810HCID 57713810, compound

Product 1

HCID 57713867HCID 57713867, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

A solution of N-[4-chloro-5-(3-hydroxy-prop-1-ynyl)-7-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl]-2,2-dimethyl-propionamide (9.0 g, 19.7 mmol) and Et3N (2 mL) in DCM (50 mL) was treated with MsCl (15.3 mL, 19.7 mmol) at 0° C. for 20 min and evaporated to give a yellow solid, containing mostly the desired mesylate (10.7 g). An aliquot of this solid (106.8 mg, 0.2 mmol) was treated with diisobutylamine (25.9 mg, 24.8 μL) in DCM (2 mL) at 0° C. for 10 h, and then at 25° C. for 3 days. Evaporation and preparative plate chromatography gave the title compound.

Workup

  1. customevaporated
  2. customto give a yellow solid
  3. customEvaporation and preparative plate chromatography

Sources & evidence

ORD record
ord-74bada0d2c034ebc99b22576ef2b50ad
Source dataset
uspto-grants-2012_01
Patent number
US08093229B2

Reaction notes

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