Ethanol → HCID 178517855, compound

HRID 1044375Notes

Reaction equation

HRID 1044375 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH2:31][CH2:30][CH2:29][C@@:16]3([C:20](=[O:21])[N:19]([C@H:22]4[CH2:27][CH2:26][C@H:25]([OH:28])[CH2:24][CH2:23]4)[CH2:18][CH2:17]3)[CH2:15]2)=[N:12][CH:13]=1.O[C@H]1CC[C@H](N2CC[C@:41]3([CH2:48][CH2:47][CH2:46][NH:45][CH2:44]3)C2=O)CC1.N1C=CC(B(O)O)=CC=1.C1(C)C=CC=CC=1.C(O)C>O.CN1C(=O)CCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N:12]1[C:11]([N:14]2[CH2:31][CH2:30][CH2:29][C@@:16]3([C:20](=[O:21])[N:19]([C@H:22]4[CH2:27][CH2:26][C@H:25]([OH:28])[CH2:24][CH2:23]4)[CH2:18][CH2:17]3)[CH2:15]2)=[CH:10][CH:9]=[C:8]([C:48]2[CH:47]=[CH:46][N:45]=[CH:44][CH:41]=2)[CH:13]=1

Participants

10

Reactant 6

HCID 702EthanolHCID 1140TolueneHCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 178517854HCID 178517854, compoundHCID 178517864HCID 178517864, compound

Product 1

HCID 178517855HCID 178517855, compound

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

Sodium carbonate (10.6 mg, 0.000100 mol) in water (0.10 mL) was added to a mixture of (5S)-7-(5-bromopyridin-2-yl)-2-(trans-4-hydroxycyclohexyl)-2,7-diazaspiro[4.5]decan-1-one (20.4 mg, 0.0000500 mol) which was prepared by using a procedure that was analogous to the one described for the synthesis of example 93 starting from (5S)-2-(trans-4-hydroxycyclohexyl)-2,7-diazaspiro[4.5]decan-1-one in NMP (0.25 mL), 4-pyridinylboronic acid (9.22 mg, 0.0000750 mol) and tetrakis(triphenylphosphine) palladium(0) (1.7 mg, 0.0000015 mol) in toluene (200.0 μL, 0.001878 mol) and ethanol (100.000 μL, 1.71267E-3 mol). The resulting mixture was heated at 120° C. for 20 min. The mixture was filtered and the filtrate was diluted with methanol and adjusted to pH=2 with TFA. The resulting solution was purified by prep.-HPLC to give the desired product. LC-MS: 407.2 (M+H)+.

Workup

  1. customwas prepared
  2. filtrationThe mixture was filtered
  3. additionthe filtrate was diluted with methanol
  4. customThe resulting solution was purified by prep.-HPLC

Sources & evidence

ORD record
ord-7c479062affa4bebbb4be47c5afb3823
Source dataset
uspto-grants-2013_10
Patent number
US08563570B2

Reaction notes

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