Diisopropylethylamine → HCID 71006843, compound

HRID 1505393Notes

Reaction equation

HRID 1505393 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@H:9]([CH2:13][CH3:14])[C:10]([OH:12])=O)=[O:7])([CH3:4])[CH3:3].C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[NH2:48][C:49]1[CH:50]=[CH:51][C:52]([O:55][C:56]2[CH:63]=[CH:62][C:59]([C:60]#[N:61])=[CH:58][C:57]=2[CH:64]2[CH2:66][CH2:65]2)=[N:53][CH:54]=1>CN(C)C=O>[C:60]([C:59]1[CH:62]=[CH:63][C:56]([O:55][C:52]2[N:53]=[CH:54][C:49]([NH:48][C:10]([C@H:9]([NH:8][C:6](=[O:7])[O:5][C:2]([CH3:1])([CH3:3])[CH3:4])[CH2:13][CH3:14])=[O:12])=[CH:50][CH:51]=2)=[C:57]([CH:64]2[CH2:65][CH2:66]2)[CH:58]=1)#[N:61]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2755936(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67237177HCID 67237177, compound2×

Product 1

HCID 71006843HCID 71006843, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

(2R)-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)butanoic acid (121.4 mg, 0.60 mmol) was dissolved in N,N-Dimethylformamide (1 mL). N,N-Diisopropylethylamine (0.126 mL, 0.72 mmol) and O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (227.2 mg, 0.60 mmol) were added. The reaction mixture was stirred at r.t. for 30 min. 4-[(5-amino-2-pyridinyl)oxy]-3-cyclopropylbenzonitrile (Intermediate 145, 100 mg) was dissolved in 1.0 mL of DMF and the obtained solution was added to the reaction mixture. The reaction mixture was stirred and heated at 60° C. for 2 h. After cooling down to r.t., the reaction mixture was evaporated under vacuum and the crude obtained was charged on a silica gel column and eluted with Cyclohexane/EtOAc (from 100:0 to 50:50 Cyclohexane/EtOAc, then plateau at 50:50) affording 133 mg of the title compound.

Workup

  1. additionthe obtained solution was added to the reaction mixture
  2. stirringThe reaction mixture was stirred
  3. temperatureheated at 60° C. for 2 h
  4. temperatureAfter cooling down to r.t.
  5. customthe reaction mixture was evaporated under vacuum
  6. customthe crude obtained
  7. additionwas charged on a silica gel column
  8. washeluted with Cyclohexane/EtOAc (from 100:0 to 50:50 Cyclohexane/EtOAc

Sources & evidence

ORD record
ord-d5a0a32fc27d473ebb3ff6f8d0e0a80a
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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