Triethylamine → HCID 86705997, compound

HRID 1408245Notes

Reaction equation

HRID 1408245 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][CH2:16][C:17]1[CH:18]=[C:19]([CH:54]=[CH:55][CH:56]=1)[C:20]([NH:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])=[CH:25][C:24]=1[C:34]1[CH:35]=[C:36]([CH:51]=[CH:52][N:53]=1)[C:37]([NH:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[C:43]([C:47]([F:50])([F:49])[F:48])[CH:42]=1)=[O:38])=[O:21].C(N(CC)CC)C.Cl[S:65]([C:68]1[CH:76]=[CH:75][C:71]([C:72]([OH:74])=[O:73])=[CH:70][CH:69]=1)(=[O:67])=[O:66]>ClCCl>[CH2:32]([N:29]([CH2:30][CH3:31])[C:26]1[CH:27]=[CH:28][C:23]([NH:22][C:20]([C:19]2[CH:18]=[C:17]([CH2:16][CH2:15][CH2:14][O:13][CH2:12][CH2:11][O:10][CH2:9][CH2:8][O:7][CH2:6][CH2:5][O:4][CH2:3][CH2:2][NH:1][S:65]([C:68]3[CH:69]=[CH:70][C:71]([C:72]([OH:74])=[O:73])=[CH:75][CH:76]=3)(=[O:67])=[O:66])[CH:56]=[CH:55][CH:54]=2)=[O:21])=[C:24]([C:34]2[CH:35]=[C:36]([C:37](=[O:38])[NH:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[C:43]([C:47]([F:48])([F:49])[F:50])[CH:42]=3)[CH:51]=[CH:52][N:53]=2)[CH:25]=1)[CH3:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 823854-(Chlorosulfonyl)benzoic acidHCID 66587995HCID 66587995, compound

Product 1

HCID 86705997HCID 86705997, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of Example 270 (200 mg, 0.25 mmol, 1.0 eq) and triethylamine (50.5, 0.50 mmol, 2.0 eq) in dichloromethane (5 mL) under N2 was cooled to 0° C. 4-(chlorosulfonyl)benzoic acid (55.15 mg, 0.25 mmol, 1.0 eq) was added and the reaction warmed to room temperature and monitored by LCMS. After 2 hours, the resulting solution was diluted with dichloromethane (20 mL) and washed with water (2×20 mL). The organic layer was acidified to pH 5 with 1N HCl and washed with water (20 mL), brine, and dried over Na2SO4. Removing the solvent resulted in 172 mg of 4-(N-(15-(3-(4-(diethylamino)-2-(4-(3-(trifluoromethyl)benzylcarbamoyl)pyridin-2-yl)phenylcarbamoyl)phenyl)-3,6,9,12-tetraoxapentadecyl)sulfamoyl)benzoic acid as an oil.

Workup

  1. washwashed with water (2×20 mL)
  2. washwashed with water (20 mL), brine
  3. dry with materialdried over Na2SO4
  4. customRemoving the solvent
  5. customresulted in 172 mg of 4-(N-(15-(3-(4-(diethylamino)-2-(4-(3-(trifluoromethyl)benzylcarbamoyl)pyridin-2-yl)phenylcarbamoyl)phenyl)-3,6,9,12-tetraoxapentadecyl)sulfamoyl)benzoic acid as an oil

Sources & evidence

ORD record
ord-861b2ec1f9ba485ba06fb8f1ced49cb3
Source dataset
uspto-grants-2014_12
Patent number
US08916569B2

Reaction notes

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