Formaldehyde → HCID 178448146, compound

HRID 539040Notes

Reaction equation

HRID 539040 reaction equation
FC(F)(F)C(O)=O.FC(F)(F)C(O)=O.[NH:15]1[CH:19]=[N:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:27]=[N:28][N:29]4[CH:34]=[CH:33][C:32]([N:35]5[C@@H:39]([CH:40]([CH3:42])[CH3:41])[CH2:38][N:37]([CH2:43][CH2:44][CH:45]6[CH2:50][CH2:49][CH2:48][NH:47][CH2:46]6)[C:36]5=[O:51])=[N:31][C:30]=34)=[CH:22][CH:21]=2)=[N:16]1.C=O.[BH4-].[Na+].O>C(#N)C>[NH:15]1[CH:19]=[N:18][C:17]([C:20]2[CH:21]=[CH:22][C:23]([C:26]3[CH:27]=[N:28][N:29]4[CH:34]=[CH:33][C:32]([N:35]5[C@@H:39]([CH:40]([CH3:42])[CH3:41])[CH2:38][N:37]([CH2:43][CH2:44][CH:45]6[CH2:50][CH2:49][CH2:48][NH:47][CH2:46]6)[C:36]5=[O:51])=[N:31][C:30]=34)=[CH:24][CH:25]=2)=[N:16]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 4311764Sodium borohydrideHCID 178448147HCID 178448147, compound

Product 1

HCID 178448146HCID 178448146, compoundYield 24.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (4S)-3-(3-(4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-isopropyl-1-(2-(piperidin-3-yl)ethyl)imidazolidin-2-one bis(2,2,2-trifluoroacetate) (Example 39; 40 mg, 0.055 mmol) in acetonitrile (2 mL) was added formaldehyde (45 mg, 37% solution in water) followed by sodium borohydride and the reaction stirred at ambient temperature for 2 hours. Water (2 mL), was added, and the reaction mixture was concentrated in vacuo. The residue purified by reverse preparative HPLC to give (4S)-3-(3-(4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-isopropyl-1-(2-(piperidin-3-yl)ethyl)imidazolidin-2-one (6.7 mg, 19%) as the mono TFA salt. LCMS (APCI+) m/z 514 [M+H]+.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe residue purified by reverse preparative HPLC

Sources & evidence

ORD record
ord-9df54b7d65ec4c40a04e70cad740901d
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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