1-Hydroxybenzotriazole → HCID 59579958, compound

HRID 2279639Notes

Reaction equation

HRID 2279639 reaction equation
F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[N:28]1[CH:33]=[CH:32][CH:31]=[N:30][C:29]=1[N:34]1[CH:38]=[C:37]([NH2:39])[C:36]([C:40]([F:43])([F:42])[F:41])=[N:35]1.C1C=CC2N(O)N=NC=2C=1.[C:54]12([CH2:64][C:65](O)=[O:66])[CH2:63][CH:58]3[CH2:59][CH:60]([CH2:62][CH:56]([CH2:57]3)[CH2:55]1)[CH2:61]2.CCN(C(C)C)C(C)C>CN(C=O)C.O>[C:54]12([CH2:64][C:65]([NH:39][C:37]3[C:36]([C:40]([F:43])([F:41])[F:42])=[N:35][N:34]([C:29]4[N:28]=[CH:33][CH:32]=[CH:31][N:30]=4)[CH:38]=3)=[O:66])[CH2:61][CH:60]3[CH2:59][CH:58]([CH2:57][CH:56]([CH2:62]3)[CH2:55]1)[CH2:63]2

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1232211-Adamantaneacetic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 59579982HCID 59579982, compound

Product 1

HCID 59579958HCID 59579958, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

BOP (35 mg, 0.08 mmol) is added to a solution of 1-pyrimidin-2-yl-3-trifluoromethyl-1H-pyrazol-4-ylamine (15 mg, 0.065 mmol), HOBt (5 mg), 1-adamantaneacetic acid (16 mg, 0.08 mmol) and DIEA (17 μL, 0.1 mmol) in DMF (0.5 mL) at RT. The mixture is stirred for 6 h. H2O is added to the mixture and is extracted with EtOAc (3×10 mL). The organic phase is dried. The crude material is purified by PTLC using 4% MeOH in CH2Cl2 to afford the title compound. 1H NMR (CDCl3): 9.38 (s, 1H), 8.6-81 (m, 2H), 7.30 (m, 1H), 2.16 (s, 2H), 2.01-1.97 (m, 3H), 1.80-1.50 (m, 12H). MS (M+1)=406.11; RT=1.4 min. *IC50.

Workup

  1. extractionis extracted with EtOAc (3×10 mL)
  2. customThe organic phase is dried
  3. customThe crude material is purified by PTLC

Sources & evidence

ORD record
ord-17d9c3924f2c4d75885f592d93624ac1
Source dataset
uspto-grants-2015_09
Patent number
US09133204B2

Reaction notes

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