Triethylamine → HCID 22291438, compound

HRID 968125Notes

Reaction equation

HRID 968125 reaction equation
CN([C:4]([O:8]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.ON1C2C=CC=[CH:34][C:29]=2[N:28]=N1.C(N(CC)CC)C.[NH2:42][C:43]([C:45]1[C:53]2[CH2:52][CH2:51][C:50]3[CH:54]=[CH:55][C:56]([NH:58][C:59](=[O:67])[C:60]4[CH:65]=[CH:64][CH:63]=[CH:62][C:61]=4[Cl:66])=[CH:57][C:49]=3[C:48]=2[N:47]([C:68]2[CH:73]=[CH:72][C:71](/[CH:74]=[CH:75]/[C:76](O)=[O:77])=[CH:70][CH:69]=2)[N:46]=1)=[O:44]>CN(C)C=O>[Cl:66][C:61]1[CH:62]=[CH:63][CH:64]=[CH:65][C:60]=1[C:59]([NH:58][C:56]1[CH:55]=[CH:54][C:50]2[CH2:51][CH2:52][C:53]3[C:45]([C:43]([NH2:42])=[O:44])=[N:46][N:47]([C:68]4[CH:73]=[CH:72][C:71](/[CH:74]=[CH:75]/[C:76]([NH:28][CH2:29][CH2:34][O:8][CH3:4])=[O:77])=[CH:70][CH:69]=4)[C:48]=3[C:49]=2[CH:57]=1)=[O:67]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22291487HCID 22291487, compound

Product 1

HCID 22291438HCID 22291438, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 4 mL peptide flask was added 100 mg of the resin. A solution of HBTU (127 mg, 0.336 mmol), 1-hydroxybenzotriazole (52 mg, 0.38 mmol), triethylamine (34 mg, 0.34 mmol), and (2E)-3-(4-{3-(aminocarbonyl)-8-[(2-chlorobenzoyl)amino]-4,5-dihydro-1H-benzo[g]indazol-1-yl}phenyl)prop-2-enoic acid (172 mg, 0.335 mmol) in 2mL of N,N-dimethylformamide was added to the resin. The peptide flask was agitated on an orbital shaker for 16 hrs, after which the solution was drained and the resin was washed with DMF, dichloromethane, and diethyl ether. The resin was dried under vacuum.

Workup

  1. washthe resin was washed with DMF, dichloromethane, and diethyl ether
  2. customThe resin was dried under vacuum

Sources & evidence

ORD record
ord-9f64affb28324717b5946e1b1cc29e75
Source dataset
uspto-grants-2005_10
Patent number
US06956052B2

Reaction notes

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