Diisopropylethylamine → HCID 59580012, compound

HRID 2279634Notes

Reaction equation

HRID 2279634 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.[F:25][C:26]([F:42])([F:41])[C:27]1[CH:32]=[CH:31][C:30]([C:33]2([CH2:39][NH2:40])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2)=[CH:29][CH:28]=1.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:40][CH2:39][C:33]2([C:30]3[CH:29]=[CH:28][C:27]([C:26]([F:25])([F:41])[F:42])=[CH:32][CH:31]=3)[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]2)=[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 59419972HCID 59419972, compoundHCID 59580025HCID 59580025, compound

Product 1

HCID 59580012HCID 59580012, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-chloro-1-pyrimidin-2-yl-1H-pyrazole-4-carboxylic acid (50 mg, 0.22 mmol) in 1.0 mL of DMF is added sequentially DIEA (0.08 mL, 0.44 mmol), 1-{1-[4-(trifluoromethyl)-phenyl]cyclohexyl}methanamine (57 mg, 0.22 mmol), and BOP (115 mg, 0.26 mmol). The resulting mixture is stirred at RT for 20 h. Water (3 mL) is added, and the mixture is filtered. The solid is washed well with water and dried in vacuo to give the title compound as a white solid. 1H NMR (400 MHz, CDCl3) δ 9.09 (1H, s), 8.78 (2H, d, J 4.8), 7.65 (2H, d, J 8.4), 7.55 (2H, d, J 8.4), 7.31 (1H, t, J 4.8), 6.27 (1H, bs), 3.63 (2H, d, J 6), 2.17 (2H, m), 1.77 (2H, m), 1.66 (2H, m), 1.42 (4H, m). MS (M+1)=464.14; RT=1.37 min. *IC50.

Workup

  1. filtrationthe mixture is filtered
  2. washThe solid is washed well with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-7dfa9ed2ebb24ad8b1f1adb65d7c3912
Source dataset
uspto-grants-2015_09
Patent number
US09133204B2

Reaction notes

Loading…