Acetic Acid → HCID 86667199, compound

HRID 2406246Notes

Reaction equation

HRID 2406246 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][CH:4]([N:8]2[CH2:13][CH2:12][N:11]3[C:14]([NH:17][S:18]([C:21]4[CH:26]=[CH:25][C:24]([NH:27][C@@H:28]([CH2:37][S:38][C:39]5[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=5)[CH2:29][CH2:30][N:31]5[CH2:36][CH2:35][O:34][CH2:33][CH2:32]5)=[C:23]([S:45]([C:48]([F:51])([F:50])[F:49])(=[O:47])=[O:46])[CH:22]=4)(=[O:20])=[O:19])=[N:15][N:16]=[C:10]3[CH2:9]2)[CH2:3][CH2:2]1.[Cl:52][C:53]1[CH:58]=[CH:57][C:56]([C:59]2[C:60]([CH:65]=O)=[CH:61][CH:62]=[CH:63][CH:64]=2)=[CH:55][CH:54]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[Cl:52][C:53]1[CH:54]=[CH:55][C:56]([C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][C:60]=2[CH2:65][N:1]2[CH2:7][CH2:6][CH2:5][CH:4]([N:8]3[CH2:13][CH2:12][N:11]4[C:14]([NH:17][S:18]([C:21]5[CH:26]=[CH:25][C:24]([NH:27][C@@H:28]([CH2:37][S:38][C:39]6[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=6)[CH2:29][CH2:30][N:31]6[CH2:32][CH2:33][O:34][CH2:35][CH2:36]6)=[C:23]([S:45]([C:48]([F:49])([F:50])[F:51])(=[O:47])=[O:46])[CH:22]=5)(=[O:19])=[O:20])=[N:15][N:16]=[C:10]4[CH2:9]3)[CH2:3][CH2:2]2)=[CH:57][CH:58]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 13936894'-Chlorobiphenyl-2-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 67980776HCID 67980776, compound

Product 1

HCID 86667199HCID 86667199, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a vial containing N-(7-azepan-4-yl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazin-3-yl)-4-((R)-3-morpholin-4-yl-1-phenylsulfanylmethyl-propylamino)-3-trifluoromethanesulfonyl-benzenesulfonamide (62 mg, 0.080 mmol) and 4′-chloro-biphenyl-2-carbaldehyde (52.1 mg, 0.241 mmol) was added methanol (2.5 mL) under nitrogen. The reaction was stirred in an ice bath for 10 minutes and then acetic acid (5.51 μL, 0.096 mmol) was added. After stirring in the ice bath for an additional 15 minutes, sodium cyanoborohydride (40.3 mg, 0.642 mmol) was added. The reaction was then allowed to warm to ambient temperature and stir for 72 hours. The reaction mixture was concentrated, filtered and purified via flash chromatography on silica gel (10-50% methanol in CH2Cl2) to afford the title compound (50 mg, 64% yield).

Workup

  1. stirringstir for 72 hours
  2. concentrationThe reaction mixture was concentrated
  3. filtrationfiltered
  4. custompurified via flash chromatography on silica gel (10-50% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-c06f963ff41547b587d8c6c4b4a324ff
Source dataset
uspto-grants-2014_08
Patent number
US08809352B2

Reaction notes

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