Diisopropylethylamine → HCID 11755651, compound

HRID 747114Notes

Reaction equation

HRID 747114 reaction equation
[CH2:1]([N:3]([CH2:35][CH3:36])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]([N:22]2[CH2:27][CH2:26][N:25]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:24][CH2:23]2)[C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16]([OH:18])=O)=[CH:8][CH:7]=1)=[O:5])[CH3:2].[CH3:37][N:38](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.CO>[CH2:1]([N:3]([CH2:35][CH3:36])[C:4]([C:6]1[CH:7]=[CH:8][C:9]([CH:12]([N:22]2[CH2:27][CH2:26][N:25]([CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH2:24][CH2:23]2)[C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16]([NH:38][CH3:37])=[O:18])=[CH:10][CH:11]=1)=[O:5])[CH3:2]

Participants

6

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 58677817HCID 58677817, compound

Product 1

HCID 11755651HCID 11755651, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution INTERMEDIATE 9 (0.120 mg, 0.25 mmol)) in 2 ml of DMF was added HATU (0.132 mg, 0.35 mmol) and diisopropylethylamine (173 μL, 0.99 mmol). The reaction was stirred for 30 minutes, after which was added (250 μL, 0.50 mmol) of 2 N HNCH3 in MeOH and the stirring continued over night. The reaction was concentrated and partitioned between a saturated solution of NaHCO3 and ethyl acetate. The organic layer was separated and the aqueous layer extracted 5 times with ethyl acetate. The organic layers were dried (MgSO4), filtered and concentrated to yield COMPOUND 3. 1H NMR (400 NM, CD3OD): δ 1.07 (m, 3H), 1.21 (m, 3H), 2.32 (m, 2H), 2.90 (s, 3H), 3.02 (m, 2H), 3.24 (m, 4H), 3.40 (m, 2H), 3.50 (m, 2H), 4.34 (s, 2H), 4.55 (s, 1H), 7.33 (d, J=8.2 Hz, 2 H), 7.41 (m, 1H), 7.48 (m, 5H), 7.56 (d, J=8.2 Hz, 2H), 7.63 (m, 2H), 7.93 (m, 1H)

Workup

  1. additionafter which was added (250 μL, 0.50 mmol) of 2 N
  2. concentrationThe reaction was concentrated
  3. custompartitioned between a saturated solution of NaHCO3 and ethyl acetate
  4. customThe organic layer was separated
  5. extractionthe aqueous layer extracted 5 times with ethyl acetate
  6. dry with materialThe organic layers were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-37740ccf10d540d696bed612897f91eb
Source dataset
uspto-grants-2008_07
Patent number
US07396834B2

Reaction notes

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