Diisopropylethylamine → HCID 86760374, compound

HRID 1376059Notes

Reaction equation

HRID 1376059 reaction equation
C(OC([N:8]1[CH:17]([C:18](=[O:52])[NH:19][CH:20]([CH2:44][C:45]2[CH:50]=[CH:49][C:48]([Cl:51])=[CH:47][CH:46]=2)[C:21]([N:23]2[CH2:28][CH2:27][N:26]([CH:29]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[F:43])[CH2:30][NH:31][C:32](=[O:36])[CH:33]([CH3:35])[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.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>>[ClH:51].[Cl:51][C:48]1[CH:47]=[CH:46][C:45]([CH2:44][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:52])[C:21]([N:23]2[CH2:24][CH2:25][N:26]([CH:29]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[F:43])[CH2:30][NH:31][C:32](=[O:36])[CH:33]([CH3:35])[CH3:34])[CH2:27][CH2:28]2)=[O:22])=[CH:50][CH:49]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69430310HCID 69430310, compound

Product 1

HCID 86760374HCID 86760374, compoundYield 42%

Procedure

3-(1-(4-Chloro-benzyl)-2-{4-[1-(2-fluoro-phenyl)-2-isobutyrylamino-ethyl]-piperazin-1-yl}-2-oxo-ethylcarbamoyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester: To a mixture of 0.26 g (0.56 mmol) of product from Preparation SM3, 0.15 g (0.51 mmol) of material from part B and 0.21 g (0.56 mmol) of O-(7-azabenzotriazole-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate in 2 ml of dichlorormethane is added 0.10 mL (0.56 mmol) of N,N-diisopropylethylamine. The mixture is stirred for 16 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) affords 0.17 g (42%) 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

Sources & evidence

ORD record
ord-b451f954a16e43e8b0bdbe80a24593b5
Source dataset
uspto-grants-2007_01
Patent number
US07169777B2

Reaction notes

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