Acetic Acid → HCID 73057222, compound

HRID 2205665Notes

Reaction equation

[C:1]([OH:4])(=O)[CH3:2].[CH:5]1[CH:6]=[CH:7][C:8]2N(O)N=[N:11][C:9]=2[CH:10]=1.CCN=C=N[CH2:20][CH2:21][CH2:22]N(C)C.Cl.[NH2:27][C@H:28]([C:38]1[O:39][C:40]([C:43]2[C:44]([O:53][CH3:54])=[N:45][C:46]3[C:51]([CH:52]=2)=[CH:50][CH:49]=[CH:48][CH:47]=3)=[CH:41][N:42]=1)[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34](=[O:37])[CH2:35][CH3:36].CCN(C(C)C)C(C)C.CN([CH:67]=[O:68])C>>[CH3:67][O:68][C:6]1[CH:7]=[C:8]2[C:9](=[CH:10][CH:5]=1)[NH:11][C:21]([CH3:22])=[C:20]2[CH2:2][C:1]([NH:27][C@H:28]([C:38]1[O:39][C:40]([C:43]2[C:44]([O:53][CH3:54])=[N:45][C:46]3[C:51]([CH:52]=2)=[CH:50][CH:49]=[CH:48][CH:47]=3)=[CH:41][N:42]=1)[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34](=[O:37])[CH2:35][CH3:36])=[O:4]

Participants

Reactant 6

HCID 176Acetic Acid

HCID 6228Dimethylformamide

HCID 757711-Hydroxybenzotriazole

HCID 81531Diisopropylethylamine

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

HCID 90036926HCID 90036926, compound

Product 1

HCID 73057222HCID 73057222, compound

Procedure

A solution of 5-methoxy-2-methyl-1H-indol-3-yl)acetic acid (1.3 eq), HOBT (1.3 eq), EDC.HCl (1.3 eq) in DMF (premixed for 3 min) was added to (S)-9-amino-9-(5-(2-methoxyquinolin-3-yl)oxazol-2-yl)nonan-3-one from the previous step (1 eq), followed by DIPEA (1.3 eq). The mixture was stirred at room temperature over night. The product was purified by preparative RP-HPLC, using water (+0.1% TFA) and MeCN (+0.1% TFA) as eluents (C18 column). MS (ES) C34H38N4O5 requires: 582.69, found: 583.

Workup

customThe product was purified by preparative RP-HPLC

Sources & evidence

ORD record: ord-aa5cec155dc04b30981d7e262b5f02d9
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371295B2

Reaction notes

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