1-Hydroxybenzotriazole → HCID 57542468, compound

HRID 2080295Notes

Reaction equation

HRID 2080295 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][CH2:6][NH:7][C:8]1[N:16]=[C:15]([C:17]2[CH:18]=[N:19][NH:20][CH:21]=2)[CH:14]=[CH:13][C:9]=1[C:10](O)=[O:11].CN(C(ON1N=[N:40][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39]C1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=[N:55][C:53]=2C=1>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][CH2:6][NH:7][C:8]1[N:16]=[C:15]([C:17]2[CH:18]=[N:19][NH:20][CH:21]=2)[CH:14]=[CH:13][C:9]=1[C:10]([NH:55][CH2:53][C:38]1[CH:39]=[N:40][CH:35]=[CH:36][CH:37]=1)=[O:11]

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57542362HCID 57542362, compound

Product 1

HCID 57542468HCID 57542468, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-(3-fluorophenethylamino)-6-(1H-pyrazol-4-yl)nicotinic acid (prepared according to example 1, method A) (1.0 g, 3.07 mmol) in DMF (10 mL) was added HBTU (1.75 g, 4.6 mmol), HOBt (0.62 g, 4.6 mmol), then amine 7 (0.66 g, 6.13 mmol). The reaction mixture was stirred at room temperature for 2 hr. The crude mixture was purified on RP-HPLC using a mixture of acetonitrile and H2O to give 2-(3-fluorophenethylamino)-6-(1H-pyrazol-4-yl)-N-(pyridin-3-ylmethyl)nicotinamide as a pale yellow solid (0.79 g, 62%). LRMS (M+H+) m/z 417.1.

Workup

  1. customThe crude mixture was purified on RP-HPLC
  2. additiona mixture of acetonitrile and H2O

Sources & evidence

ORD record
ord-91a033c9c80d47d7868cb56ccd002a65
Source dataset
uspto-grants-2011_04
Patent number
US07932270B2

Reaction notes

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