1,5-Naphthalenedisulfonic acid → HCID 11355034, compound

HRID 2109673Notes

Reaction equation

HRID 2109673 reaction equation
[OH:1][C@H:2]([C:36]1[CH:45]=[CH:44][C:43]([OH:46])=[C:42]2[C:37]=1[CH:38]=[CH:39][C:40](=[O:47])[NH:41]2)[CH2:3][NH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][CH:17]([O:20][C:21](=[O:35])[NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:16][CH2:15]1.[C:48]1([S:62]([OH:65])(=[O:64])=[O:63])[C:57]2[CH:56]=[CH:55][CH:54]=[C:53]([S:58]([OH:61])(=[O:60])=[O:59])[C:52]=2[CH:51]=[CH:50][CH:49]=1>CO>[C:48]1([S:62]([OH:65])(=[O:64])=[O:63])[C:57]2[CH:56]=[CH:55][CH:54]=[C:53]([S:58]([OH:61])(=[O:60])=[O:59])[C:52]=2[CH:51]=[CH:50][CH:49]=1.[OH:1][C@H:2]([C:36]1[CH:45]=[CH:44][C:43]([OH:46])=[C:42]2[C:37]=1[CH:38]=[CH:39][C:40](=[O:47])[NH:41]2)[CH2:3][NH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][CH:17]([O:20][C:21](=[O:35])[NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:18][CH2:19]1

Participants

4

Reactant 2

HCID 66661,5-Naphthalenedisulfonic acidHCID 9874175HCID 9874175, compound

Product 1

HCID 11355034HCID 11355034, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
30 °C

Procedure

Biphenyl-2-ylcarbamic acid 1-{9-[(R)-2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino]nonyl}piperidin-4-yl ester (1.0 g, 1.56 mmol, free base) was dissolved in methanol (10 mL; low water content). A solution of naphthalene-1,5-disulfonic acid (0.45 g, 1.56 mmol) in methanol (5 mL; low water content) was added and the reaction mixture was stirred at 30° C. for two hours and then at room temperature overnight (18 h). The resulting thick slurry was filtered and the filtrate cake was washed with methanol (5 mL) and then dried to give the title compound (1.16 g, 80% yield) as off-white crystalline solid.

Workup

  1. customat room temperature
  2. customovernight (18 h)
  3. filtrationThe resulting thick slurry was filtered
  4. washthe filtrate cake was washed with methanol (5 mL)
  5. customdried

Sources & evidence

ORD record
ord-9174ebe6ca4542d68c27614a613c4106
Source dataset
uspto-grants-2009_04
Patent number
US07514558B2

Reaction notes

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