1-Hydroxybenzotriazole → HCID 58101721, compound

HRID 1517379Notes

Reaction equation

HRID 1517379 reaction equation
[CH:1]1([N:4]([CH2:18][C:19](O)=[O:20])[S:5]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH3:16])=[CH:10][C:9]=2[CH3:17])(=[O:7])=[O:6])[CH2:3][CH2:2]1.[NH2:22][C:23]1[C:32]([NH2:33])=[CH:31][CH:30]=[CH:29][C:24]=1[C:25]([O:27][CH3:28])=[O:26].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>>[NH2:22][C:23]1[C:32]([NH:33][C:19](=[O:20])[CH2:18][N:4]([CH:1]2[CH2:2][CH2:3]2)[S:5]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH3:16])=[CH:10][C:9]=2[CH3:17])(=[O:6])=[O:7])=[CH:31][CH:30]=[CH:29][C:24]=1[C:25]([O:27][CH3:28])=[O:26]

Participants

6

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 5718252,3-Diaminobenzoic acid methyl esterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58101637HCID 58101637, compound

Product 1

HCID 58101721HCID 58101721, compoundYield 75%

Procedure

2-(N-Cyclopropyl-4-methoxy-2,6-dimethylphenylsulfonamido)acetic acid was reacted with methyl 2,3-diaminobenzoate (1.3 eq.) in the presence of EDCl (1 eq.), HOBT (1 eq.) and DIPEA (10 eq.) and the desired product thereby formed was employed directly in the next stage without further working up. Yield: 75%

Sources & evidence

ORD record
ord-410ab9639890429faeaf6bbc354de944
Source dataset
uspto-grants-2012_07
Patent number
US08232288B2

Reaction notes

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