1,2-Dichloroethane → N-[(1R)-1-[(Benzylsulfonyl)methyl]-2-{[(1S)-1-methyl-2-{[4-(trifluoromethoxy)phenyl]amino}ethyl]amino}-2-oxoethyl]morpholine-4-carboxamide

HRID 2249950Notes

Reaction equation

HRID 2249950 reaction equation
[N:1]1([C:7]([NH:9][C@@H:10]([CH2:14][S:15]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:17])=[O:16])[C:11]([OH:13])=O)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[F:25][C:26]([F:40])([F:39])[O:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][CH2:35][C@@H:36]([NH2:38])[CH3:37])=[CH:30][CH:29]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C(Cl)Cl>[CH3:37][C@H:36]([NH:38][C:11]([C@@H:10]([NH:9][C:7]([N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)=[O:8])[CH2:14][S:15]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:17])=[O:16])=[O:13])[CH2:35][NH:34][C:31]1[CH:30]=[CH:29][C:28]([O:27][C:26]([F:25])([F:39])[F:40])=[CH:33][CH:32]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 11439693(R)-2-[(morpholine-4-carbonyl)-amino]-3-phenylmethanesulfonyl-propionic acidHCID 59733160HCID 59733160, compound

Product 1

HCID 9547980N-[(1R)-1-[(Benzylsulfonyl)methyl]-2-{[(1S)-1-methyl-2-{[4-(trifluoromethoxy)phenyl]amino}ethyl]amino}-2-oxoethyl]morpholine-4-carboxamideYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(R)-[(Morpholine-4-carbonyl)-amino]-3-phenylmethanesulfonyl-propionic acid (73 mg, 0.21 mmol, 1.0 eq.), N1-(4-Trifluoromethoxy-phenyl)-(S)-propane-1,2-diamine from Scheme 1a (48 mg, 0.21 mmol, 1.0 eq.), EDC (59 mg, 0.31 mmol, 1.5 eq.), and HOBT (38 mg, 0.25 mmol, 1.2 eq.) were dissolved in CH2Cl2 at room temperature. N-methylmorpholine (225 μL, 2.05 mmol, 10 eq.) was added via syringe and the reaction was monitored to completion by LC/MS. The solvent was evaporated and the reaction was purified by mass-directed HPLC and provided 44 mg (0.06 mmol, 31%) of a off-white solid as a mono-TFA salt: HPLC-MS calcd. for C25H31F3N4O6S (M+H+) 573.2. found 573.3.

Workup

  1. customThe solvent was evaporated
  2. customthe reaction was purified by mass-directed HPLC

Sources & evidence

ORD record
ord-9fc8da570b0f4fd9aecd49e14bce698e
Source dataset
uspto-grants-2008_01
Patent number
US07314872B2

Reaction notes

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