Diisopropylethylamine → HCID 59579816, compound

HRID 2279636Notes

Reaction equation

HRID 2279636 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][C:26]1[N:31]=[CH:30][C:29]([C:32]2([CH2:38][NH2:39])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[CH:28][CH:27]=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:39][CH2:38][C:32]2([C:29]3[CH:30]=[N:31][C:26]([CH3:25])=[CH:27][CH:28]=3)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]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 59580025HCID 59580025, compoundHCID 68735930HCID 68735930, compound

Product 1

HCID 59579816HCID 59579816, 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), 1-[1-(6-methylpyridin-3-yl)-cyclohexyl]methanamine (67 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 9.18 (1H, s), 8.90 (2H, d, J 4), 8.43 (1H, s), 8.03 (1H, s), 7.64 (1H, d, J 8), 7.56 (1H, s), 7.18 (1H, d, J 7.6), 2.41 (3H, s), 2.13 (2H, m), 1.56 (5H, m), 1.22 (5H, m). MS (M+1)=411.18; RT=1.08 min. *IC50.

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-8ec37f5bf4f34be682b711e9e320933f
Source dataset
uspto-grants-2015_09
Patent number
US09133204B2

Reaction notes

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