Citric Acid → HCID 118094089, compound

HRID 515532Notes

Reaction equation

HRID 515532 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:25]1([NH2:30])[CH2:29][CH2:28][CH2:27][CH2:26]1.[CH3:31][C:32]1[C:36]([C:37]2[CH:38]=[C:39]([S:47]([NH:50][CH:51]3[CH2:55][CH2:54][CH2:53][CH:52]3[C:56](O)=[O:57])(=[O:49])=[O:48])[C:40]3[CH:41]=[CH:42][CH:43]=[N:44][C:45]=3[CH:46]=2)=[C:35]([CH3:59])[O:34][N:33]=1.CCN(C(C)C)C(C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[CH:25]1([NH:30][C:56]([C@H:52]2[CH2:53][CH2:54][CH2:55][C@H:51]2[NH:50][S:47]([C:39]2[C:40]3[CH:41]=[CH:42][CH:43]=[N:44][C:45]=3[CH:46]=[C:37]([C:36]3[C:32]([CH3:31])=[N:33][O:34][C:35]=3[CH3:59])[CH:38]=2)(=[O:49])=[O:48])=[O:57])[CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

7

Reactant 5

HCID 311Citric AcidHCID 2906CyclopentylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 131733299HCID 131733299, compound

Product 1

HCID 118094089HCID 118094089, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of HATU (38 mg, 0.10 mmol), cyclopentanamine (9 mg, 0.10 mmol), and 1S,2R)-2-(7-(3,5-dimethylisoxazol-4-yl)quinoline-5-sulfonamido)cyclopentanecarboxylic acid (21 mg, 0.05 mmol) in anhydrous DMF (1 mL), was added slowly Hunig's base (30 uL, 0.16 mmol) with stirring until the starting material acid disappeared (about 1 hr). The reaction mixture was acidified with aqueous citric acid to pH 2-3, then subjected to preparative HPLC to give (1S,2R)—N-cyclopentyl-2-(7-(3,5-dimethylisoxazol-4-yl)quinoline-5-sulfonamido)cyclopentanecarboxamide.

Workup

  1. custom(about 1 hr)

Sources & evidence

ORD record
ord-a849d74d11c34d8e9bbbc5ea1101a41b
Source dataset
uspto-grants-2015_08
Patent number
US09108953B2

Reaction notes

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