Diisopropylethylamine → HCID 86592915, compound

HRID 1376057Notes

Reaction equation

HRID 1376057 reaction equation
C(OC([N:8]1[CH:17]([C:18](=[O:50])[NH:19][CH:20]([CH2:42][C:43]2[CH:48]=[CH:47][C:46]([Cl:49])=[CH:45][CH:44]=2)[C:21]([N:23]2[CH2:28][CH2:27][N:26]([CH:29]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[F:41])[CH2:30][NH:31][C:32](=[O:34])[CH3:33])[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:49].[C:32]([NH:31][CH2:30][CH:29]([N:26]1[CH2:27][CH2:28][N:23]([C:21](=[O:22])[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:50])[CH2:42][C:43]2[CH:48]=[CH:47][C:46]([Cl:49])=[CH:45][CH:44]=2)[CH2:24][CH2:25]1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[F:41])(=[O:34])[CH3:33]

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 69434090HCID 69434090, compound

Product 1

HCID 86592915HCID 86592915, compoundYield 52%

Procedure

3-[2-{4-[2-Acetylamino-1-(2-fluoro-phenyl)-ethyl]-piperazin-1-yl}-1-(4-chloro-benzyl)-2-oxo-ethylcarbamoyl]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester: To a mixture of 0.28 g (0.62 mmol) of product from Preparation SM3, 0.15 g (0.57 mmol) of material from part B and 0.24 g (0.62 mmol) of O-(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) afforded 0.23 g (52%) 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-54f0fd4529974ffd9dbefe29e5014b16
Source dataset
uspto-grants-2007_01
Patent number
US07169777B2

Reaction notes

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