Diisopropylethylamine → HCID 68291526, compound

HRID 73044Notes

Reaction equation

HRID 73044 reaction equation
[CH:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][C:6]=1[CH3:14])([CH3:3])[CH3:2].Cl.[C:16]1([CH:22]2[O:27][C:26]3([CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)[CH2:25][NH:24][C:23]2=[O:33])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([N:30]2[CH2:29][CH2:28][C:26]3([CH2:25][NH:24][C:23](=[O:33])[CH:22]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[O:27]3)[CH2:32][CH2:31]2)=[O:11])=[CH:7][C:6]=1[CH3:14])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 592729354-Isopropoxy-3-methylbenzoic acidHCID 68290960HCID 68290960, compound

Product 1

HCID 68291526HCID 68291526, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 4-isopropoxy-3-methyl-benzoic acid (114 mg, 0.59 mmol), 4-phenyl-5-oxa-2,9-diazaspiro[5.5]undecan-3-one hydrochloride salt (166 mg, 0.59 mmol) and HATU (223 mg, 0.59 mmol) in DMF (0.5 mL) was added diisopropylethylamine (228 mg, 307 μL, 1.76 mmol) and the reaction mixture was stirred for 16 hours. The reaction mixture was concentrated in vacuo, diluted with methanol and purified by prep LCMS (1-99% ACN/H2O, 5 mM HCl modifier) to give 3-(4-isopropoxy-3-methyl-benzoyl)-8-phenyl-7-oxa-3,10-diazaspiro[5.5]undecan-9-one (100 mg, 40%) as a yellow foam. ESI-MS m/z calc. 422.2. Found 423.5 (M+1)+; Retention time: 1.61 minutes (3 min run).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with methanol
  3. custompurified by prep LCMS (1-99% ACN/H2O, 5 mM HCl modifier)

Sources & evidence

ORD record
ord-21326c3c75094984822df09ffd0980a2
Source dataset
uspto-grants-2014_09
Patent number
US08828996B2

Reaction notes

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