Diisopropylethylamine → HCID 58994339, compound

HRID 1190229Notes

Reaction equation

HRID 1190229 reaction equation
[C:1]([Si:5]([CH3:32])([CH3:31])[O:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([C:23]3[CH2:28][CH2:27][C:26]([CH3:30])([CH3:29])[CH2:25][CH:24]=3)[CH:17]=2)[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[K+].[C:34]([C:36]1[N:37]=[C:38]([C:49]([O-])=[O:50])[N:39]([CH2:41][O:42][CH2:43][CH2:44][Si:45]([CH3:48])([CH3:47])[CH3:46])[CH:40]=1)#[N:35].C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:1]([Si:5]([CH3:32])([CH3:31])[O:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:49]([C:38]3[N:39]([CH2:41][O:42][CH2:43][CH2:44][Si:45]([CH3:48])([CH3:47])[CH3:46])[CH:40]=[C:36]([C:34]#[N:35])[N:37]=3)=[O:50])=[C:18]([C:23]3[CH2:28][CH2:27][C:26]([CH3:30])([CH3:29])[CH2:25][CH:24]=3)[CH:17]=2)[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 58994510HCID 58994510, compoundHCID 67188357potassium 4-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carboxylate

Product 1

HCID 58994339HCID 58994339, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-piperazin-1-ylmethyl}-2-(4,4-dimethyl-cyclohex-1-enyl)-phenylamine (as prepared in the previous step, 233 mg, 0.590 mmol) in CH2Cl2 (10 mL) was treated with 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylate potassium salt (as prepared in Example 1, step (d), 188 mg, 0.610 mmol), PyBroP (332 mg, 0.713 mmol), and DIEA (177 μL, 10.2 mmol) at RT for 1 h. The mixture was diluted with CH2Cl2 (40 mL) and washed with water (1×30 mL) and satd aq NaHCO3 (1×30 mL). The combined aqueous layers were extracted with CH2Cl2 (1×30 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo. Purification of the residue on a 20-g Isolute SPE column on a FlashMaster system with 10-25% EtOAc-hexane afforded the title compound (223 mg, 62%) as an off-white solid. Mass spectrum (ESI, m/z): Calcd. for C38H62N6O3Si2, 707.4 (M+H). found 707.4.

Workup

  1. washwashed with water (1×30 mL)
  2. extractionThe combined aqueous layers were extracted with CH2Cl2 (1×30 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue on a 20-g Isolute SPE column on a FlashMaster system with 10-25% EtOAc-hexane

Sources & evidence

ORD record
ord-94e15b9da1344dfba287f10f97560318
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

Loading…