Diisopropylethylamine → HCID 59579999, compound

HRID 2279624Notes

Reaction equation

HRID 2279624 reaction equation
[CH3:1][O:2][C:3]1[C:7]([C:8]([OH:10])=O)=[CH:6][N:5]([C:11]2[N:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[N:4]=1.CCN(C(C)C)C(C)C.[C:26]12([CH2:36][NH2:37])[CH2:35][CH:30]3[CH2:31][CH:32]([CH2:34][CH:28]([CH2:29]3)[CH2:27]1)[CH2:33]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:26]12([CH2:36][NH:37][C:8]([C:7]3[C:3]([O:2][CH3:1])=[N:4][N:5]([C:11]4[N:16]=[CH:15][CH:14]=[CH:13][N:12]=4)[CH:6]=3)=[O:10])[CH2:33][CH:32]3[CH2:31][CH:30]([CH2:29][CH:28]([CH2:34]3)[CH2:27]1)[CH2:35]2

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 86625Tricyclo(3.3.1.13,7)dec-1-ylmethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 59579844HCID 59579844, compound

Product 1

HCID 59579999HCID 59579999, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-methoxy-1-pyrimidin-2-yl-1H-pyrazole-4-carboxylic acid (40 mg, 0.18 mmol) in 1.0 mL of DMF is added sequentially DIEA (0.063 mL, 0.36 mmol), 1-adamantan-1-ylmethan-amine (30 mg, 0.18 mmol) and BOP (97 mg, 0.22 mmol). The resulting mixture is stirred at RT for 18 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 to give a brown solid. Purification by column chromatography (gradient from 80% EtOAc/Hex to EtOAc) affords the title compound as a pale brown solid. 1H NMR (400 MHz, CDCl3) δ 9.02 (1H, s), 8.74 (2H, d, J 4.8), 7.19 (1H, t, J 4.8), 6.88 (1H, bs), 4.24 (3H, s), 3.12 (2H, d, J 6.4), 2.00 (3H, bs), 1.60 (12H, m). MS (M+1)=368.07; RT=1.65 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. customto give a brown solid
  6. customPurification by column chromatography (gradient from 80% EtOAc/Hex to EtOAc)

Sources & evidence

ORD record
ord-5a15df9259cc450d911ed91de8302369
Source dataset
uspto-grants-2015_09
Patent number
US09133204B2

Reaction notes

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