Diisopropylethylamine → HCID 178453004, compound

HRID 529741Notes

Reaction equation

HRID 529741 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[C:17]([C:18]([OH:20])=O)=[C:12]2[N:13]=[CH:14][CH:15]=[CH:16][N:11]2[N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:54][C:55]1[CH:56]=[CH:57][C:58]([O:67][CH:68]([F:70])[F:69])=[C:59]([C:61]2[NH:65][N:64]=[CH:63][C:62]=2[NH2:66])[CH:60]=1>CN(C=O)C.O>[Cl:54][C:55]1[CH:56]=[CH:57][C:58]([O:67][CH:68]([F:70])[F:69])=[C:59]([C:61]2[C:62]([NH:66][C:18]([C:17]3[C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[N:10][N:11]4[CH:16]=[CH:15][CH:14]=[N:13][C:12]=34)=[O:20])=[CH:63][NH:64][N:65]=2)[CH:60]=1

Participants

7

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 66851504HCID 66851504, compoundHCID 118522324HCID 118522324, compound

Product 1

HCID 178453004HCID 178453004, compoundYield 76,939.602%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of compound 2-tert-butoxycarbonylamino-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (2.78 g, 0.01 mol) in DMF (40 mL) was added DIPEA (3.9 g, 0.03 mol), HATU (3.8 g, 0.01 mol) and 5-(5-chloro-2-difluoromethoxyphenyl)-1H-pyrazol-4-ylamine (2.6 g, 0.01 mmol), and the reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into water and the precipitate was collected to give the target compound as a solid (4 g, 77%). LCMS (Method 7) [M+Na]+=541.9, RT=1.20 min. 1H NMR (400 MHz, DMSO-d6) δ: (ppm) 13.13 (s, 1H), 9.58 (s, 2H), 9.2 (dd, 1H, J=7.2, 1.6 Hz), 8.58 (d, 1H, J=2), 8.27 (s, 1H), 7.60 (m, 2H), 7.23-7.04 (m, 3H), 1.48 (s, 9H).

Workup

  1. customthe precipitate was collected

Sources & evidence

ORD record
ord-b4de891ecfbd4187bac92a7221c89e9b
Source dataset
uspto-grants-2016_05
Patent number
US09346815B2

Reaction notes

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