Diisopropylethylamine → HCID 59579864, compound

HRID 2279630Notes

Reaction equation

HRID 2279630 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.[C:25]12([CH2:35][NH2:36])[CH2:34][CH:29]3[CH2:30][CH:31]([CH2:33][CH:27]([CH2:28]3)[CH2:26]1)[CH2:32]2.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>[C:25]12([CH2:35][NH:36][C:7]([C:6]3[C:2]([Cl:1])=[N:3][N:4]([C:10]4[N:15]=[CH:14][CH:13]=[CH:12][N:11]=4)[CH:5]=3)=[O:9])[CH2:32][CH:31]3[CH2:30][CH:29]([CH2:28][CH:27]([CH2:33]3)[CH2:26]1)[CH2:34]2

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 86625Tricyclo(3.3.1.13,7)dec-1-ylmethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 59580025HCID 59580025, compound

Product 1

HCID 59579864HCID 59579864, 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-adamantan-1-ylmethan-amine (36 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 extracted with CH2Cl2 (5 mL). The CH2Cl2 layer is dried (Na2SO4), filtered, and evaporated in vacuo. The residue is purified by silica gel column chromatography (gradient from 30% EtOAc/hexane to 60% EtOAc/hexane) to give the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 9.31 (1H, s), 8.91 (2H, d, J 4.8), 8.18 (1H, bs), 7.56 (1H, t, J 4.8), 2.92 (2H, d, J 5.6), 1.92 (3H, s), 1.60 (6H, m), 1.47 (6H, s). MS (M+1)=372.18; RT=1.35 min. *IC50.

Workup

  1. extractionthe mixture is extracted with CH2Cl2 (5 mL)
  2. dry with materialThe CH2Cl2 layer is dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue is purified by silica gel column chromatography (gradient from 30% EtOAc/hexane to 60% EtOAc/hexane)

Sources & evidence

ORD record
ord-647b729aff8b4b99a9dca6b9ded7daaf
Source dataset
uspto-grants-2015_09
Patent number
US09133204B2

Reaction notes

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