1-Hydroxybenzotriazole → HCID 57507349, compound

HRID 556501Notes

Reaction equation

HRID 556501 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([NH:11][C:12]2([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=3)[C:20]3[C:15](=[CH:16][C:17]([Cl:21])=[CH:18][CH:19]=3)[NH:14][C:13]2=[O:22])[CH:3]=1.[NH:31]1[CH2:36][CH2:35][CH2:34][C@H:33]([NH:37][C:38](=[O:40])[CH3:39])[CH2:32]1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>ClCCl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:31]2[CH2:36][CH2:35][CH2:34][C@H:33]([NH:37][C:38](=[O:40])[CH3:39])[CH2:32]2)=[O:7])=[C:4]([NH:11][C:12]2([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=3)[C:20]3[C:15](=[CH:16][C:17]([Cl:21])=[CH:18][CH:19]=3)[NH:14][C:13]2=[O:22])[CH:3]=1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 7175793HCID 7175793, compoundHCID 574790864-Bromo-2-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-ylamino]-benzoic acid

Product 1

HCID 57507349HCID 57507349, compoundYield 17.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The mixture 4-Bromo-2-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-ylamino]-benzoic acid (150 mg, 0.298 mmol), (S)-N-Piperidin-3-yl-acetamide (63 mg, 0.446 mmol), EDC.HCl (85 mg, 0.446 mmol), HOBt (60 mg, 0.446 mmol) and DIPEA (154 mg, 1.190 mmol) in dichloro-methane (2 mL) was stirred at room temperature for overnight. The crude was then purified with Prep-HPLC to give 33 mg N-((S)-1-{4-Bromo-2-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-ylamino]-benzoyl}-piperidin-3-yl)-acetamide as yellow solid.

Workup

  1. customThe crude was then purified with Prep-HPLC

Sources & evidence

ORD record
ord-2e119c47912b432e9e151143e59acc93
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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