Diisopropylethylamine → HCID 117774183, compound

HRID 2279637Notes

Reaction equation

HRID 2279637 reaction equation
[Cl:1][C:2]1[C:6]([C:7]([OH:9])=O)=[CH:5][N:4]([C:10]2[N:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[N:3]=1.CCN(C(C)C)C(C)C.[CH3:25][CH:26]([CH3:37])[CH2:27][CH:28](C1C=NC=CC=1)[CH2:29][NH2:30].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C.O>[Cl:1][C:2]1[C:6]([C:7]([NH:30][CH2:29][CH2:28][CH2:27][C:26](=[CH2:25])[CH3:37])=[O:9])=[CH:5][N:4]([C:10]2[N:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[N:3]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 55265072HCID 55265072, compoundHCID 59580025HCID 59580025, compound

Product 1

HCID 117774183HCID 117774183, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-chloro-1-pyrimidin-2-yl-1H-pyrazole-4-carboxylic acid (75 mg, 0.33 mmol) in 1.0 mL of DMF is added sequentially DIEA (0.11 mL, 0.66 mmol), 4-methyl-2-pyridin-3-yl-pentan-1-amine (59 mg, 0.33 mmol), and BOP (177 mg, 0.40 mmol). The resulting mixture is stirred at RT for 20 h. Water (3 mL) is added, and the mixture is extracted with EtOAc (5 mL). The EtOAc layer is dried (Na2SO4), filtered, and evaporated in vacuo. The residue is purified by preparative chromatography (2% MeOH/CH2Cl2) to give the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 9.13 (1H, s), 8.89 (2H, d, J 4.8), 8.39 (3H, m), 7.67 (1H, d, J 7.6), 7.55 (1H, t, J 4.4), 7.32 (1H, m), 3.43 (1H, m), 3.32 (1H, m), 2.99 (1H, bs), 1.58 (1H, m), 1.50 (1H, m), 1.25 (1H, m), 0.81 (6H, d, J 6). MS (M+1)=385.09; RT=1.25 min.

Workup

  1. extractionthe mixture is extracted with EtOAc (5 mL)
  2. dry with materialThe EtOAc layer is dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue is purified by preparative chromatography (2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-a3ec22dbee3645ea93b5ac7a25d67336
Source dataset
uspto-grants-2015_09
Patent number
US09133204B2

Reaction notes

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