Triethylamine → HCID 86590028, compound

HRID 2415788Notes

Reaction equation

HRID 2415788 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH:13][C:14]1[CH:15]=[CH:16][C:17]3[O:23][CH2:22][CH2:21][CH2:20][N:19]([CH2:24][C:25]([OH:27])=O)[C:18]=3[CH:28]=1)=[O:12])=[CH:5]2.[NH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>C1COCC1>[O:27]=[C:25]([N:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1)[CH2:24][N:19]1[C:18]2[CH:28]=[C:14]([NH:13][C:11]([C:6]3[NH:7][C:8]4[C:4]([CH:5]=3)=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=4)=[O:12])[CH:15]=[CH:16][C:17]=2[O:23][CH2:22][CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 22636752HCID 22636752, compound

Product 1

HCID 86590028HCID 86590028, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

{2-[(5-Chloro-1H-indole-2-carbonyl)-amino]-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl}-acetic acid (80 mg) and pyrrolidine (14.2 mg) were dissolved in anhydrous THF. To that solution was added BOP and the resulting mixture treated with triethylamine (40.5 mg). The reaction was stirred overnight at room temperature. The reaction was evaportated and the crude product purified by TLC using EtOAc as solvent to yield 68 mg of the product. LCMS: AP+ 453/455.

Workup

  1. customthe crude product purified by TLC

Sources & evidence

ORD record
ord-4136d8e90f1a48818ff3eb423c353026
Source dataset
uspto-grants-2004_11
Patent number
US06821977B2

Reaction notes

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