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Diisopropylethylamine → HCID 59579856, compound

HRID 2279632
Notes
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Reaction equation

HRID 2279632 reaction equation
[Cl:1][C:2]1[N:6]([C:7]2[N:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[N:5]=[CH:4][C:3]=1[C:13]([OH:15])=O.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:13]([C:3]3[CH:4]=[N:5][N:6]([C:7]4[N:8]=[CH:9][CH:10]=[CH:11][N:12]=4)[C:2]=3[Cl:1])=[O:15])[CH2:32][CH:31]3[CH2:30][CH:29]([CH2:28][CH:27]([CH2:33]3)[CH2:26]1)[CH2:34]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 86625Tricyclo(3.3.1.13,7)dec-1-ylmethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 59579909HCID 59579909, compound

Product 1

HCID 59579856HCID 59579856, compound

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-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 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 reddish/brown oil. Purification by silica gel column chromatography (gradient from 90% EtOAc/hexane to EtOAc) affords the title compound as a light reddish/brown solid. 1H NMR (400 MHz, CDCl3) δ 8.89 (2H, d, J 4.8), 8.28 (1H, s), 7.41 (1H, t, J 4.8), 6.47 (1H, bs), 3.18 (2H, d, J 6), 2.01 (3H, s), 1.69 (6H, m), 1.58 (6H, s). MS (M+1)=372.19; RT=1.31 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 reddish/brown oil
  6. customPurification by silica gel column chromatography (gradient from 90% EtOAc/hexane to EtOAc)

Sources & evidence

ORD record
ord-f495da4ebf854eff9c8560c39baa36c2
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09133204B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes