4-[[(1R)-3-(4-Morpholinyl)-1-[(phenylthio)methyl]propyl]amino]-3-[(trifluoromethyl)sulfonyl]benzenesulfonamide → (R)-(4'-chlorobiphenyl-2-yl)(1-(4-(4-((R)-4-morpholino-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)phenylsulfonylcarbamoyl)phenyl)piperidin-4-yl)methyl methyl hydrogen phosphate, hydrochloride salt

HRID 1771250Notes

Reaction equation

HRID 1771250 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C@H:14]([O:30][P:31]([O:35][CH3:36])([O:33]C)=[O:32])[CH:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][CH:22]=3)[CH2:17][CH2:16]2)=[CH:4][CH:3]=1.[O:37]1[CH2:42][CH2:41][N:40]([CH2:43][CH2:44][C@@H:45]([NH:54][C:55]2[CH:60]=[CH:59][C:58]([S:61]([NH2:64])(=[O:63])=[O:62])=[CH:57][C:56]=2[S:65]([C:68]([F:71])([F:70])[F:69])(=[O:67])=[O:66])[CH2:46][S:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH2:39][CH2:38]1>ClCCCl>[ClH:1].[P:31]([OH:33])([O:35][CH3:36])([O:30][C@@H:14]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[CH:15]1[CH2:16][CH2:17][N:18]([C:21]2[CH:22]=[CH:23][C:24]([C:25](=[O:26])[NH:64][S:61]([C:58]3[CH:59]=[CH:60][C:55]([NH:54][C@H:45]([CH2:44][CH2:43][N:40]4[CH2:41][CH2:42][O:37][CH2:38][CH2:39]4)[CH2:46][S:47][C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)=[C:56]([S:65]([C:68]([F:70])([F:71])[F:69])(=[O:67])=[O:66])[CH:57]=3)(=[O:62])=[O:63])=[CH:28][CH:29]=2)[CH2:19][CH2:20]1)=[O:32]

Participants

4

Reactant 2

HCID 250584544-[[(1R)-3-(4-Morpholinyl)-1-[(phenylthio)methyl]propyl]amino]-3-[(trifluoromethyl)sulfonyl]benzenesulfonamide2×HCID 58080233(R)-4-(4-((4'-chlorobiphenyl-2-yl)(dimethoxyphosphoryloxy)methyl)piperidin-1-yl)benzoic acid2×

Product 1

HCID 131732791(R)-(4'-chlorobiphenyl-2-yl)(1-(4-(4-((R)-4-morpholino-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)phenylsulfonylcarbamoyl)phenyl)piperidin-4-yl)methyl methyl hydrogen phosphate, hydrochloride salt

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A mixture of (R)-4-(4-((4′-chlorobiphenyl-2-yl)(dimethoxyphosphoryloxy)methyl)piperidin-1-yl)benzoic acid (INTERMEDIATE 122, 57.4 mg, 0.11 mmol), (R)-4-(4-morpholino-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)benzenesulfonamide (INTERMEDIATE 69, 60 mg, 0.11 mmol), EDC (41.6 mg, 0.22 mmol), TEA (0.03 ml, 0.22 mmol), and DCE (2 ml) were stirred at r.t. for 4 days. The volatiles were removed under reduced pressure and the concentrate was purified by reverse phase HPLC according to the following conditions:

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe concentrate was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-3175f17b3d214f548c8648fa7b3bede5
Source dataset
uspto-grants-2016_02
Patent number
US09248140B2

Reaction notes

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