Diisopropylethylamine → HCID 71006843, compound

HRID 527732Notes

Reaction equation

HRID 527732 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, compound

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 (Reference Intermediate R24, 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-f06ab5a3e99f4336a08b133fa4f26746
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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