1-Hydroxybenzotriazole → HCID 73057537, compound

HRID 2205674Notes

Reaction equation

HRID 2205674 reaction equation
[NH2:1][C@H:2]([C:12]1[O:13][C:14]([C:17]2[C:18](=[O:28])[N:19]([CH3:27])[C:20]3[C:25]([CH:26]=2)=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:15][N:16]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:11])[CH2:9][CH3:10].[S:29]1[C:33]([C:34](O)=[O:35])=[CH:32][N:31]=[CH:30]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:27][N:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:26]=[C:17]([C:14]2[O:13][C:12]([C@@H:2]([NH:1][C:34]([C:33]3[S:29][CH:30]=[N:31][CH:32]=3)=[O:35])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:11])[CH2:9][CH3:10])=[N:16][CH:15]=2)[C:18]1=[O:28]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 84494Thiazole-5-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 90036335HCID 90036335, compound

Product 1

HCID 73057537HCID 73057537, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-3-(2-(1-amino-7-oxononyl)oxazol-5-yl)-1-methylquinolin-2(1 H)-one (1 eq), prepared as described in steps 1 to 5 of Example 7, was treated with a solution of thiazole-5-carboxylic acid (1.3 eq), HOBT (1.3 eq) and EDC.HCl (1.3 eq) in DMF (premixed for 3 min), followed by DIPEA (1.3 eq). The mixture was stirred at room temperature for 2 h and the desired product was isolated by preparative RP-HPLC, using water (+0.01% TFA) and MeCN (+0.01% TFA) as eluents (column C18). The pooled product fractions were lyophilized and the product was obtained as a white solid. MS (ES) C26H28N4O4S requires: 492.59, found: 493. 1H-NMR (400 MHz, DMSO-d6) δ: 9.28 (1 H, d, J=8 Hz), 9.26 (1 H, s), 8.62 (1 H, s), 8.29 (1 H, s), 7.91 (1 H, d, J=7.6 Hz), 7.84 (1 H, s), 7.68 (1 H, t, J=7.2 Hz), 7.61 (1 H, d, J=8.2 Hz), 7.34 (1 H, t, J=7.6 Hz), 5.27-5.22 (1 H, m), 3.75 (3 H, s), 2.39-2.36 (4 H, m), 2.09-2.06 (1 H, m), 2.00-1.96 (1H, m), 1.50-1.27 (6 H, m), 0.89 (3 H, t, J=7.2 Hz).

Sources & evidence

ORD record
ord-956ab822cba94e70b833c759c64cb639
Source dataset
uspto-grants-2016_06
Patent number
US09371295B2

Reaction notes

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