Triethylamine → HCID 57501775, compound

HRID 601541Notes

Reaction equation

HRID 601541 reaction equation
[CH:1]([Si:4]([CH:35]([CH3:37])[CH3:36])([CH:32]([CH3:34])[CH3:33])[N:5]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][C:15]([C:17]3[S:21][C:20]([C:22]4[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=4)=[N:19][C:18]=3[CH2:29][CH2:30]O)=[O:16])=[CH:11][CH:12]=2)[CH:7]=[CH:6]1)([CH3:3])[CH3:2].CCN(CC)CC>C(Cl)Cl.CCOC(C)=O.CS(Cl)(=O)=O>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([C:20]2[S:21][C:17]3[C:15](=[O:16])[N:14]([C:10]4[CH:9]=[C:8]5[C:13](=[CH:12][CH:11]=4)[N:5]([Si:4]([CH:35]([CH3:37])[CH3:36])([CH:1]([CH3:2])[CH3:3])[CH:32]([CH3:34])[CH3:33])[CH:6]=[CH:7]5)[CH2:30][CH2:29][C:18]=3[N:19]=2)=[CH:23][CH:24]=1

Participants

6

Reactant 2

HCID 8471Triethylamine2×HCID 57870256HCID 57870256, compound

Product 1

HCID 57501775HCID 57501775, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 31297Methanesulfonyl chlorideCatalyst2×HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 2-(4-chloro-phenyl)-4-(2-hydroxy-ethyl)-thiazole-5-carboxylic acid (1-triisopropylsilanyl-1H-indol-5-yl)-amide in CH2Cl2 (25 mL) and add Et3N (0.33 mL, 2.36 mmol) and methanesulfonyl chloride (0.16 mmol, 2.13 mmol). Stir the mixture at room temperature for 2 h, then add additional Et3N (0.33 mL, 2.36 mmol) and methanesulfonyl chloride (0.16 mmol, 2.13 mmol). Stir the mixture for an additional 2 h, dilute with EtOAc (50 mL), then wash with water (20 mL) and brine (20 mL). Dry, filter and concentrate the organic solution then and purify the crude material by flash chromatography, using a linear gradient of 100% hexanes to 50% EtOAc/hexanes as eluent, to give the title compound (1.15 g, 100%). MS (ES+) 536.1 (M+1)+. 1H NMR (400 MHz, CDCl3) δ: 7.93 (d, 2H, J=8.3 Hz), 7.56 (d, 1H, J=1.8 Hz), 7.50 (d, 1H, J=8.8 Hz), 7.44 (d, 2H, J=8.3 Hz), 7.27 (d, 1H, J=3.1 Hz), 7.14-7.10 (m, 1H), 6.61 (d, 1H, J=2.6 Hz), 4.16 (t, 2H, J=6.8 Hz), 3.29 (t, 2H, J=7.0 Hz), 1.73-1.65 (m, 3H), 1.14 (d, 18H, J=7.5 Hz).

Workup

  1. stirringStir the mixture for an additional 2 h
  2. washwash with water (20 mL) and brine (20 mL)
  3. customDry
  4. filtrationfilter
  5. concentrationconcentrate the organic solution
  6. custompurify the crude material by flash chromatography

Sources & evidence

ORD record
ord-50744ccf2fb54b88a6390aa79b519d89
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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