Methanesulfonic Acid → HCID 49833441, compound

HRID 1047136Notes

Reaction equation

HRID 1047136 reaction equation
C(OC([NH:8][CH:9]1[CH2:13][CH2:12][N:11]([C:14]2[N:23]=[C:22]3[C:17]([C:18](=[O:34])[C:19]([C:31]([OH:33])=[O:32])=[CH:20][N:21]3[C@@H:24]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:25][OH:26])=[CH:16][C:15]=2[C:35]2[CH:36]=[N:37][C:38]([NH:50][C:51]([NH:53][CH2:54][CH3:55])=[O:52])=[CH:39][C:40]=2[C:41]2[S:42][CH:43]=[C:44]([C:46]([F:49])([F:48])[F:47])[N:45]=2)[CH2:10]1)=O)(C)(C)C.CS(O)(=O)=O>ClCCl>[NH2:8][CH:9]1[CH2:13][CH2:12][N:11]([C:14]2[N:23]=[C:22]3[C:17]([C:18](=[O:34])[C:19]([C:31]([OH:33])=[O:32])=[CH:20][N:21]3[C@@H:24]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:25][OH:26])=[CH:16][C:15]=2[C:35]2[CH:36]=[N:37][C:38]([NH:50][C:51]([NH:53][CH2:54][CH3:55])=[O:52])=[CH:39][C:40]=2[C:41]2[S:42][CH:43]=[C:44]([C:46]([F:49])([F:48])[F:47])[N:45]=2)[CH2:10]1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 68751365HCID 68751365, compound2×

Product 1

HCID 49833441HCID 49833441, compoundYield 11.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 7-(3-(tert-butoxycarbonylamino)pyrrolidin-1-yl)-6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1-((S)-1-hydroxy-3,3-dimethylbutan-2-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid (Intermediate 105) (290 mg, 0.37 mmol, 1 equiv.) in dichloromethane (2 mL) was added methanesulfonic acid (0.048 mL, 0.73 mmol, 2 equiv.). The reaction was stirred at 23° C. for 2 h. The reaction was concentrated and re-suspended in water. The precipitate was discarded, and the filtrate was concentrated. The compound was purified via C18 silica gel chromatography and concentrated to afford 7-(3-aminopyrrolidin-1-yl)-6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1-((5)-1-hydroxy-3,3-dimethylbutan-2-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid (28.7 mg, 11%).

Workup

  1. concentrationThe reaction was concentrated
  2. concentrationthe filtrate was concentrated
  3. customThe compound was purified via C18 silica gel chromatography
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-afe5dc67d1324e34a2f4d71ba0c6b80b
Source dataset
uspto-grants-2013_10
Patent number
US08569484B2

Reaction notes

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