Diisopropylethylamine → HCID 67058658, compound

HRID 470329Notes

Reaction equation

HRID 470329 reaction equation
[NH2:1][C:2]1[C:6]([C:7]([OH:9])=O)=[CH:5][N:4]([C:10]2[N:19]=[CH:18][C:17]3[CH2:16][CH2:15][C:14]4[CH:20]=[C:21]([O:24][CH3:25])[CH:22]=[CH:23][C:13]=4[C:12]=3[N:11]=2)[N:3]=1.C[N:27](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.ClC1N=CC2CCC3C=C(OC)C=CC=3C=2N=1>CN(C=O)C>[NH2:1][C:2]1[C:6]([C:7]([NH2:27])=[O:9])=[CH:5][N:4]([C:10]2[N:19]=[CH:18][C:17]3[CH2:16][CH2:15][C:14]4[CH:20]=[C:21]([O:24][CH3:25])[CH:22]=[CH:23][C:13]=4[C:12]=3[N:11]=2)[N:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 53486023HCID 53486023, compoundHCID 59784811HCID 59784811, compound

Product 1

HCID 67058658HCID 67058658, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-amino-1-(8-methoxy-5,6-dihydrobenzo[h]quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid 1 (0.084 g, 0.25 mmol), HBTU (0.113 g, 0.3 mmol) and DIEA (0.18 mL, 1 mmol) in DMF (1 mL) was added amine 2 (0.3 mmol). Resulting reaction mixture was stirred at room temperature for 18 h. After completion of the reaction, solvent was removed on rotavap and residue was purified by preparative HPLC to give 3-amino-1-(8-methoxy-5,6-dihydrobenzo[h]quinazolin-2-yl)-1H-pyrazole-4-carboxylic amide 3.

Workup

  1. customResulting
  2. customreaction mixture
  3. customAfter completion of the reaction, solvent
  4. customwas removed on rotavap
  5. customresidue was purified by preparative HPLC

Sources & evidence

ORD record
ord-5675d275e85b44a2824e69cfb11a3781
Source dataset
uspto-grants-2014_01
Patent number
US08629147B2

Reaction notes

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