1-Hydroxybenzotriazole → HCID 73057225, compound

HRID 2205668Notes

Reaction equation

HRID 2205668 reaction equation
[NH2:1][C@H:2]([C:12]1[O:13][C:14]([C:17]2[C:18]([O:27][CH3:28])=[N:19][C:20]3[C:25]([CH:26]=2)=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:15][N:16]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:11])[CH2:9][CH3:10].[CH3:29][O:30][C:31]1[CH:32]=[C:33]2[C:37](=[CH:38][CH:39]=1)[NH:36][C:35]([CH3:40])=[C:34]2[CH2:41][C:42](O)=[O:43].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C>CN(C=O)C.O.CC#N>[CH3:29][O:30][C:31]1[CH:32]=[C:33]2[C:37](=[CH:38][CH:39]=1)[NH:36][C:35]([CH3:40])=[C:34]2[CH2:41][C:42]([NH:1][C@H:2]([C:12]1[O:13][C:14]([C:17]2[C:18]([O:27][CH3:28])=[N:19][C:20]3[C:25]([CH:26]=2)=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:15][N:16]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:11])[CH2:9][CH3:10])=[O:43]

Participants

9

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 761515-Methoxy-2-methylindole-3-acetic acidHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 90036254HCID 90036254, compound

Product 1

HCID 73057225HCID 73057225, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

(S)-9-amino-9-(5-(2-methoxyquinolin-3-yl)-1,3,4-oxadiazol-2-yl)nonan-3-one (0.05 mmol, 1 eq), prepared as described above, was treated with a solution of (5-methoxy-2-methyl-1H-indol-3-yl)acetic 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 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) C33H37N5O5 requires: 583.68, found: 584.

Workup

  1. customthe product was isolated by preparative RP-HPLC
  2. customthe product was obtained as a white solid

Sources & evidence

ORD record
ord-374a2e4418b948b7aac195e57cab520a
Source dataset
uspto-grants-2016_06
Patent number
US09371295B2

Reaction notes

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