Diisopropylethylamine → HCID 16037880, compound

HRID 1160185Notes

Reaction equation

HRID 1160185 reaction equation
[NH2:1][C:2]1([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:6][CH2:5][O:4][CH:3]1[O:7][CH2:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([N:18]([S:22]([CH3:25])(=[O:24])=[O:23])[CH2:19][CH2:20][CH3:21])[CH:17]=1)[C:12]([OH:14])=O.C([N:36](CC)[CH:37]([CH3:39])[CH3:38])(C)C.CN([P+](ON1N=N[C:55]2[CH:56]=[CH:57][CH:58]=C[C:54]1=2)(N(C)C)N(C)C)C.[F:62][P-](F)(F)(F)(F)F>CN(C=O)C>[NH2:1][C:2]1([CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:6][CH2:5][O:4][CH:3]1[O:7][CH2:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([N:18]([S:22]([CH3:25])(=[O:23])=[O:24])[CH2:19][CH2:20][CH3:21])[CH:17]=1)[C:12]([NH:36][C@@H:37]([C:38]1[CH:58]=[CH:57][C:56]([F:62])=[CH:55][CH:54]=1)[CH3:39])=[O:14]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 67423285HCID 67423285, compound

Product 1

HCID 16037880HCID 16037880, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-{[(3-amino-3-benzyltetrahydrofuran-2-yl)oxy]methyl}-5-[(methylsulfonyl)(propyl)amino]benzoic acid (25 mg, 0.04 mmol), 4-fluoro-R-alpha-methyl-benzyl amine (10 mg, 0.08 mmol), N,N-diisopropylethylamine (0.02 mL, 0.11 mmol), BOP reagent (25 mg, 0.06 mmol) in DMF (0.6 mL) is stirred at RT for 20 min and purified by preparative HPLC (5->95% CH3CN/H2O, 0.1% added TFA, C18 Sunfire Waters, 30×150 mm) to give 3-{[(3-amino-3-benzyltetrahydrofuran-2-yl)oxy]methyl}-N-[(1R)-1-(4-fluorophenyl)ethyl]-5-[(methylsulfonyl)(propyl)amino]benzamide (2 diastereoisomer separated). MS M+1=584.

Workup

  1. custompurified by preparative HPLC (5->95% CH3CN/H2O, 0.1% added TFA, C18 Sunfire Waters, 30×150 mm)

Sources & evidence

ORD record
ord-225e430d9f22410faf8607f2753acde0
Source dataset
uspto-grants-2010_10
Patent number
US07816378B2

Reaction notes

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