Diisopropylethylamine → HCID 86592916, compound

HRID 1376058Notes

Reaction equation

HRID 1376058 reaction equation
C(OC([N:8]1[CH:17]([C:18](=[O:51])[NH:19][CH:20]([CH2:43][C:44]2[CH:49]=[CH:48][C:47]([Cl:50])=[CH:46][CH:45]=2)[C:21]([N:23]2[CH2:28][CH2:27][N:26]([CH:29]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[F:42])[CH2:30][NH:31][C:32](=[O:35])[CH2:33][CH3:34])[CH2:25][CH2:24]2)=[O:22])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=O)(C)(C)C.C(N(CC)C(C)C)(C)C>>[ClH:50].[Cl:50][C:47]1[CH:46]=[CH:45][C:44]([CH2:43][CH:20]([NH:19][C:18]([CH:17]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][NH:8]2)=[O:51])[C:21]([N:23]2[CH2:24][CH2:25][N:26]([CH:29]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[F:42])[CH2:30][NH:31][C:32](=[O:35])[CH2:33][CH3:34])[CH2:27][CH2:28]2)=[O:22])=[CH:49][CH:48]=1

Participants

3

Reactant 2

HCID 81531DiisopropylethylamineHCID 69430875HCID 69430875, compound

Product 1

HCID 86592916HCID 86592916, compoundYield 53%

Procedure

3-(1-(4-Chloro-benzyl)-2-{4-[1-(2-fluoro-phenyl)-2-propionylamino-ethyl]-piperazin-1-yl}-2-oxo-ethylcarbamoyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester: To a mixture of 0.30 g (0.65 mmol) of the product from Preparation SM3, 0.17 g (0.59 mmol) of material from part B and 0.25 g (0.65 mmol) of 0-(7-azabenzotriazole-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate in 2 ml of dichlorormethane is added 0.11 mL (0.62 mmol) of N,N-diisopropylethylamine. The mixture is stirred for three hr and washed with 10% aqueous sodium bisulfate. After the organic portion is separated, the aqueous portion is saturated with sodium chloride and extracted three times with dichloromethane. The combined organics are dried (Na2SO4), filtered and concentrated in vacuo. Chromatography (Biotage, 5% ethanol, ethyl acetate) of the residue affords a mixture which is chromatographed again (Biotage, 0.25% NH4OH/2.25% methanol/dichloromethane) affords 0.23 g (53%) of the title compound.

Workup

  1. washwashed with 10% aqueous sodium bisulfate
  2. customAfter the organic portion is separated
  3. extractionextracted three times with dichloromethane
  4. dry with materialThe combined organics are dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customChromatography (Biotage, 5% ethanol, ethyl acetate) of the residue affords a mixture which
  8. customis chromatographed again (Biotage, 0.25% NH4OH/2.25% methanol/dichloromethane)

Sources & evidence

ORD record
ord-dac6a8fdf78942c8a8fa061c75843e86
Source dataset
uspto-grants-2007_01
Patent number
US07169777B2

Reaction notes

Loading…