1-Hydroxybenzotriazole → HCID 57542266, compound

HRID 2080288Notes

Reaction equation

HRID 2080288 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[C:11]([NH:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)[N:10]=1)#[N:2].[NH2:28][CH2:29][C@@H:30]1[NH:34][C:33](=[O:35])[CH2:32][CH2:31]1.C1C=CC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:17]=[CH:16][C:12]([C:13]([NH:28][CH2:29][C@H:30]2[CH2:31][CH2:32][C:33](=[O:35])[NH:34]2)=[O:15])=[C:11]([NH:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)[N:10]=1)#[N:2]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22865792(5R)-5-(Aminomethyl)pyrrolidin-2-oneHCID 575423046-(2-Cyanophenyl)-2-(3-fluorophenethylamino)nicotinic acid

Product 1

HCID 57542266HCID 57542266, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinic acid (110 mg, 0.30 mmol), (R)-5-(aminomethyl)pyrrolidin-2-one (52 mg, 0.46 mmol), HOBT (62 mg, 0.46 mmol), and HBTU (174 mg, 0.46 mg) in RB flask was added DMF and the mixture was stirred at r.t. for 1 h. LC/MS indicated the reaction was complete and the mixture was filtered and purified on RP-HPLC using a mixture of acetonitrile and water to give (R)-6-(2-cyanophenyl)-2-(3-fluorophenethylamino)-N-((5-oxopyrrolidin-2-yl)methyl)nicotinamide (91.6 mg, 67%). LRMS (M+H+) m/z 458.1.

Workup

  1. filtrationthe mixture was filtered
  2. custompurified on RP-HPLC
  3. additiona mixture of acetonitrile and water

Sources & evidence

ORD record
ord-52a3b52111b14ee18f21bde286660be6
Source dataset
uspto-grants-2011_04
Patent number
US07932270B2

Reaction notes

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