Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → 5-(Aminosulfonyl)-N1-{(1S,2R)-1-benzyl-2-hydroxy-3-[(3-methoxybenzyl)amino]propyl}-N3,N-dipropylisophthalamide

HRID 1350968Notes

Reaction equation

HRID 1350968 reaction equation
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:12]2N=CC=[CH:16][C:11]=2N=N1.[NH2:25][S:26]([C:29]1[CH:30]=[C:31]([CH:35]=[C:36]([C:38]([N:40](CCC)[CH2:41][CH2:42][CH3:43])=[O:39])[CH:37]=1)[C:32](O)=[O:33])(=[O:28])=[O:27].FC(F)(F)C(O)=O.[NH2:54][C@@H:55]([CH2:69][C:70]1[CH:75]=[C:74](F)[CH:73]=[C:72](F)[CH:71]=1)[C@H:56]([OH:68])[CH2:57][NH:58][CH2:59][C:60]1[CH:65]=[CH:64][CH:63]=[C:62]([O:66][CH3:67])[CH:61]=1>CN(C=O)C>[NH2:25][S:26]([C:29]1[CH:37]=[C:36]([C:38]([NH:40][CH2:41][CH2:42][CH3:43])=[O:39])[CH:35]=[C:31]([CH:30]=1)[C:32]([N:54]([C@@H:55]([CH2:69][C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1)[C@H:56]([OH:68])[CH2:57][NH:58][CH2:59][C:60]1[CH:65]=[CH:64][CH:63]=[C:62]([O:66][CH3:67])[CH:61]=1)[CH2:12][CH2:11][CH3:16])=[O:33])(=[O:27])=[O:28]

Participants

5

Reactant 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 225936363-(Aminosulfonyl)-5-[(dipropylamino)-carbonyl]benzoic acidHCID 69869154(2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-methoxybenzyl)amino]-2-butanol Trifluoroacetate

Product 1

HCID 686094725-(Aminosulfonyl)-N1-{(1S,2R)-1-benzyl-2-hydroxy-3-[(3-methoxybenzyl)amino]propyl}-N3,N-dipropylisophthalamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

O—(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, 0.0928 g, 0.244 mmol) is added to a mixture of, 3-(aminosulfonyl)-5-[(dipropylamino)-carbonyl]benzoic acid (XXXIX, PREPARATION 13, 0.0800 g, 0.244 mmol) and (2R,3S)-3-amino-1-[(3-methoxybenzyl)-amino]-4-phenyl-2-butanol (VIII, EXAMPLE 175, 0.0732 g, 0.244 mmol) in dry DMF (3 mL). The mixture is stirred for 18 hours at 20–25 degrees, and then partitioned between ethyl acetate and water. The organic phase is separated and washed with saline, dried over anhydrous sodium sulfate, filtered and concentrated. The concentrate is column chouromatographed (silica gel; methanol/dichloromethane, 5/95) to give the title compound, MS (ESI+) for C32H42N4O6S m/z (M+H)+=611.5; HRMS (FAB) calculated for C32H42N4O6S +H1=611.2903, found=611.2904.

Workup

  1. custompartitioned between ethyl acetate and water
  2. customThe organic phase is separated
  3. washwashed with saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bf8410b7972444cda229af4fad031ec0
Source dataset
uspto-grants-2007_05
Patent number
US07214715B2

Reaction notes

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