Triethylamine → HCID 90022221, compound

HRID 1529248Notes

Reaction equation

HRID 1529248 reaction equation
[C:1]12([N:11]=[C:12]=[O:13])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15]1.CCN(CC)CC>C(Cl)Cl>[C:1]12([NH:11][C:12]([N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH2:16][CH2:15]3)=[O:13])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10328IndolineHCID 20599951-Isocyanatoadamantane

Product 1

HCID 90022221HCID 90022221, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 35.7 mg (0.2 mmol) 1-adamantyl isocyanate, 20 mg (0.168 mmol) indoline and 51 mg (0.5 mmol) NEt3 in 2 mL DCM was shaken at room temperature overnight and evaporated to dryness. The residue was taken up in DMF and subjected to column chromatography on reversed phase eluting with a gradient formed from acetonitrile, water and formic acid to yield after evaporation of the product containing fractions 15.2 mg (30%) of the title compound as white solid. MS(m/e): 297.4 (MH+).

Workup

  1. customevaporated to dryness
  2. washeluting with a gradient
  3. customformed from acetonitrile, water and formic acid
  4. customto yield
  5. customafter evaporation of the product
  6. additioncontaining fractions 15.2 mg (30%) of the title compound as white solid

Sources & evidence

ORD record
ord-0f42437d6ad94ef39a52ba257a99b062
Source dataset
uspto-grants-2015_07
Patent number
US09090615B2

Reaction notes

Loading…