Dimethylformamide → 2-Hydroxy-N-methyl-2-[6-{[4-(trifluoromethoxy)phenyl]sulfonyl}-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepin-8-yl]acetamide

HRID 1691477Notes

Reaction equation

HRID 1691477 reaction equation
[OH:1][CH:2]([C:6]1[CH:7]=[CH:8][C:9]2[NH:15][C:14]3[N:16]=[C:17]([C:20]([F:23])([F:22])[F:21])[CH:18]=[CH:19][C:13]=3[CH2:12][N:11]([S:24]([C:27]3[CH:32]=[CH:31][C:30]([O:33][C:34]([F:37])([F:36])[F:35])=[CH:29][CH:28]=3)(=[O:26])=[O:25])[C:10]=2[CH:38]=1)C(O)=O.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN.Cl.C(N(C(C)C)CC)(C)C.[CH3:78][N:79]([CH:81]=[O:82])C>>[OH:1][CH:2]([C:6]1[CH:7]=[CH:8][C:9]2[NH:15][C:14]3[N:16]=[C:17]([C:20]([F:22])([F:23])[F:21])[CH:18]=[CH:19][C:13]=3[CH2:12][N:11]([S:24]([C:27]3[CH:32]=[CH:31][C:30]([O:33][C:34]([F:35])([F:36])[F:37])=[CH:29][CH:28]=3)(=[O:25])=[O:26])[C:10]=2[CH:38]=1)[C:81]([NH:79][CH3:78])=[O:82]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 6364545Methylamine hydrochlorideHCID 59618708Hydroxy[6-{[4-(trifluoromethoxy)phenyl]sulfonyl}-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepin-8-yl]acetic acid

Product 1

HCID 596187292-Hydroxy-N-methyl-2-[6-{[4-(trifluoromethoxy)phenyl]sulfonyl}-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepin-8-yl]acetamide

Procedure

A mixture of hydroxy[6-{[4-(trifluoromethoxy)phenyl]sulfonyl}-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepin-8-yl]acetic acid (51 mg, 0.091 mmol, Example 513), BOP (60.1 mg, 0.136 mmol), MeNH2—HCl (12.2 mg, 0.181 mmol), and diisopropylethylamine (0.08 ml, 0.453 mmol) in DMF was stirred for 2.5 h at rt. LC-MS showed the reaction complete. The solution was concentrated and the residue was purified by mass-directed HPLC eluting with H2O/MeCN/TFA (90:10:0.1-10:90:0.1) to give the title compound; Mass Spectrum: m/e=576 (M+1).

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue was purified by mass-directed HPLC
  3. washeluting with H2O/MeCN/TFA (90:10:0.1-10:90:0.1)

Sources & evidence

ORD record
ord-b23621d9c7254bc5bdbf09f59a046736
Source dataset
uspto-grants-2012_04
Patent number
US08153626B2

Reaction notes

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