Triethylamine → HCID 59077557, compound

HRID 1359852Notes

Reaction equation

HRID 1359852 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][S:10]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])/[C:16]/2=[CH:23]\[C:24]1[NH:28][C:27]([CH3:29])=[C:26]([CH2:30][C:31](O)=[O:32])[C:25]=1[CH3:34])(=[O:12])=[O:11].C(N(CC)CC)C.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.[F:69][CH:70]1[CH2:75][CH2:74][N:73]([CH2:76][CH2:77][NH2:78])[CH2:72][CH2:71]1>CN(C=O)C>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[CH2:9][S:10]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])/[C:16]/2=[CH:23]\[C:24]1[NH:28][C:27]([CH3:29])=[C:26]([CH2:30][C:31]([NH:78][CH2:77][CH2:76][N:73]2[CH2:74][CH2:75][CH:70]([F:69])[CH2:71][CH2:72]2)=[O:32])[C:25]=1[CH3:34])(=[O:12])=[O:11]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 121500682-(4-Fluoropiperidin-1-YL)ethanamineHCID 59077497HCID 59077497, compound

Product 1

HCID 59077557HCID 59077557, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of {5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl}-acetic acid (156 mg, 0.3 mmol), triethylamine (0.084 mL, 0.6 mmol) and BOP reagent (199 mg, 0.45 mmol) in DMF (0.5 mL) was added 2-(4-fluoro-piperidin-1-yl)-ethylamine (48 mg, 0.32 mmol) in DMF (0.5 mL). The mixture was stirred at rt for overnight. After the usual workup, the residue was purified on a silica gel column to give 110 mg (57%) of the titled compound. MS m/z 645 [M−1].

Workup

  1. customAfter the usual workup, the residue was purified on a silica gel column

Sources & evidence

ORD record
ord-118c7c6272ef49e2be9bd85d9fbd0a03
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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