Acetic Acid → 3,5-Dichloro-4-((S)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-((S)-3-(3-(2-(3-((phenylamino)methyl)benzamido)ethylcarbamoyl)phenylsulfonyl)-thiazolidine-2-carbonyloxy)ethyl)pyridine 1-oxide

HRID 520343Notes

Reaction equation

HRID 520343 reaction equation
[Cl:1][C:2]1[CH:3]=[N+:4]([O-:59])[CH:5]=[C:6]([Cl:58])[C:7]=1[CH2:8][C@@H:9]([C:43]1[CH:48]=[CH:47][C:46]([O:49][CH:50]([F:52])[F:51])=[C:45]([O:53][CH2:54][CH:55]2[CH2:57][CH2:56]2)[CH:44]=1)[O:10][C:11]([C@H:13]1[N:17]([S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27](=[O:42])[NH:28][CH2:29][CH2:30][NH:31][C:32](=[O:41])[C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([CH:39]=O)[CH:34]=3)[CH:22]=2)(=[O:20])=[O:19])[CH2:16][CH2:15][S:14]1)=[O:12].[NH2:60][C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[N+:4]([O-:59])[CH:5]=[C:6]([Cl:58])[C:7]=1[CH2:8][C@@H:9]([C:43]1[CH:48]=[CH:47][C:46]([O:49][CH:50]([F:51])[F:52])=[C:45]([O:53][CH2:54][CH:55]2[CH2:57][CH2:56]2)[CH:44]=1)[O:10][C:11]([C@H:13]1[N:17]([S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27](=[O:42])[NH:28][CH2:29][CH2:30][NH:31][C:32](=[O:41])[C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([CH2:39][NH:60][C:61]4[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=4)[CH:34]=3)[CH:22]=2)(=[O:20])=[O:19])[CH2:16][CH2:15][S:14]1)=[O:12]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6115AnilineHCID 5049666Sodium triacetoxyborohydrideHCID 1185584603,5-Dichloro-4-((S)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(((S)-3-((3-((2-(3-formylbenzamido)ethyl)carbamoyl)phenyl)sulfonyl)thiazolidine-2-carbonyl)oxy)ethyl)pyridine 1-oxide

Product 1

HCID 1185584733,5-Dichloro-4-((S)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-((S)-3-(3-(2-(3-((phenylamino)methyl)benzamido)ethylcarbamoyl)phenylsulfonyl)-thiazolidine-2-carbonyloxy)ethyl)pyridine 1-oxideYield 107%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3,5-Dichloro-4-((S)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(((S)-3-((3-((2-(3-formylbenzamido)ethyl)carbamoyl)phenyl)sulfonyl)thiazolidine-2-carbonyl)oxy)ethyl)pyridine 1-oxide (30 mg, 0.034 mmol) was dissolved in DCM (300 μl, 4.66 mmol). Aniline (3.75 mg, 0.040 mmol) and acetic Acid (2.306 μl, 0.040 mmol) were added, and the mixture was stirred at RT for 30′. Sodium triacetoxyborohydride (8.54 mg, 0.040 mmol) was added, and the mixture was stirred at room temperature for 8 hrs to achieve completion. The reaction mixture was diluted with DCM and extracted with water. The organic phase was dried over Na2SO4 and concentrated under vacuum to give 3,5-dichloro-4-((S)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(((S)-3-((3-((2-(3-((phenylamino)methyl)benzamido)ethyl)carbamoyl)phenyl)-sulfonyl)thiazolidine-2-carbonyl)oxy)ethyl)pyridine 1-oxide (35 mg, 0.036 mmol, 107% yield).

Workup

  1. stirringthe mixture was stirred at room temperature for 8 hrs
  2. extractionextracted with water
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a66e8596f70c47719e6a8390e57415f9
Source dataset
uspto-grants-2016_05
Patent number
US09326976B2

Reaction notes

Loading…