Triethylamine → HCID 86705002, compound

HRID 513028Notes

Reaction equation

HRID 513028 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:8]2[CH2:12][C@@H:11]([OH:13])[CH2:10][N:9]2[C:14]2[CH:19]=[CH:18][N:17]3[N:20]=[CH:21][C:22]([C:23]([N:25]([CH2:35][C:36]4[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=4)[CH2:26][C:27]4[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=4)=[O:24])=[C:16]3[CH:15]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH3:51][S:52](Cl)(=[O:54])=[O:53]>C(Cl)Cl>[CH3:51][S:52]([O:13][C@@H:11]1[CH2:12][C@H:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)[N:9]([C:14]2[CH:19]=[CH:18][N:17]3[N:20]=[CH:21][C:22]([C:23](=[O:24])[N:25]([CH2:26][C:27]4[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=4)[CH2:35][C:36]4[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=4)=[C:16]3[CH:15]=2)[CH2:10]1)(=[O:54])=[O:53]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 682826095-((2R,4R)-2-(3-fluorophenyl)-4-hydroxypyrrolidin-1-yl)-N,N-bis(4-methoxybenzyl)pyrazolo[1,5-a]pyridine-3-carboxamide

Product 1

HCID 86705002HCID 86705002, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution 5-((2R,4R)-2-(3-fluorophenyl)-4-hydroxypyrrolidin-1-yl)-N,N-bis(4-methoxybenzyl)pyrazolo[1,5-a]pyridine-3-carboxamide (I-33) (150 mg, 0.26 mmol) in DCM (anhyd, 2 mL) at 0° C. was added triethylamine (0.070 mL, 0.5 mmol) followed by dropwise addition of methanesulfonyl chloride (28 μL, 0.36 mmol). After stirring 2 hours at room temperature the reaction mixture was concentrated under reduced pressure. The resulting solid was taken up in EtOAc and washed twice with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to afford (3R,5R)-1-(3-(bis(4-methoxybenzyl)carbamoyl)pyrazolo[1,5-a]pyridin-5-yl)-5-(3-fluorophenyl)pyrrolidin-3-yl methanesulfonate (I-34), which was used without further purification. MS m/z 659.2 (M+1)+.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. washwashed twice with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-28c77c666c594db2aa59b0d523702eea
Source dataset
uspto-grants-2015_08
Patent number
US09102671B2

Reaction notes

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