Dichloromethane → HCID 86666512, compound

HRID 1426363Notes

Reaction equation

HRID 1426363 reaction equation
[N:1]1([CH:7]2[CH2:10][C:9]([CH2:33][C:34]#[N:35])([N:11]3[CH:15]=[C:14]([C:16]4[C:17]5[CH:24]=[CH:23][N:22]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:18]=5[N:19]=[CH:20][N:21]=4)[CH:13]=[N:12]3)[CH2:8]2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(Cl)Cl.[F:39][C:40]([F:50])([F:49])[CH:41]([N:46]=[C:47]=[O:48])[C:42]([F:45])([F:44])[F:43].C1(C)C=CC=C(C)C=1.C(N(CC)C(C)C)(C)C>C(OCC)(=O)C>[C:34]([CH2:33][C:9]1([N:11]2[CH:15]=[C:14]([C:16]3[C:17]4[CH:24]=[CH:23][N:22]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:31])([CH3:30])[CH3:32])[C:18]=4[N:19]=[CH:20][N:21]=3)[CH:13]=[N:12]2)[CH2:8][CH:7]([N:1]2[CH2:2][CH2:3][N:4]([C:47]([NH:46][CH:41]([C:40]([F:39])([F:50])[F:49])[C:42]([F:44])([F:43])[F:45])=[O:48])[CH2:5][CH2:6]2)[CH2:10]1)#[N:35]

Participants

7

Reactant 5

HCID 6344DichloromethaneHCID 7929M-XyleneHCID 81531DiisopropylethylamineHCID 125481321,1,1,3,3,3-Hexafluoro-2-isocyanatopropaneHCID 69675374HCID 69675374, compound

Product 1

HCID 86666512HCID 86666512, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of {3-piperazin-1-yl-1-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclobutyl}acetonitrile (0.10 g, 0.20 mmol) in methylene chloride (5 mL, 80 mmol) was added. 0.21M 1,1,1,3,3,3-hexafluoro-2-isocyanatopropane in m-xylene (1.2 mL, 0.24 mmol) was added, followed by N,N-diisopropylethylamine (71 μL, 0.41 mmol). The reaction was stirred overnight. The reaction was rotovaped and ethyl acetate was added, washed with sat. NH4Cl (×2), sat. NaHCO3, and sat. NaCl. The extracts were dried and the solvent removed by rotary evaporation to give 164 mg of an orange oil. The crude oil was purified by column chromatography on 40 g silica gel using a gradient of 0-8% MeOH/DCM, 0-0.8% NH4Cl. The product was collected as 82 mg of a glass (59% yield). LCMS (M+1): 586.

Workup

  1. washwashed with sat. NH4Cl (×2), sat. NaHCO3, and sat. NaCl
  2. customThe extracts were dried
  3. customthe solvent removed by rotary evaporation

Sources & evidence

ORD record
ord-910c294137ce4dfabe527065641d041c
Source dataset
uspto-grants-2015_01
Patent number
US08933085B2

Reaction notes

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