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 1783228노트

반응식

HRID 1783228 반응식
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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, 0.0928 9, 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.

후처리

  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

출처 및 근거

ORD 기록
ord-357b9e9632e94076a4cb47c31f35dba0
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07498436B2

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