Triethylamine → HCID 178508579, compound

HRID 1010704Notes

Reaction equation

HRID 1010704 reaction equation
C(N(CC)CC)C.FC(F)(F)C(O)=O.[Cl:15][C:16]1[CH:28]=[CH:27][CH:26]=[CH:25][C:17]=1[O:18][CH2:19][C@H:20]1[CH2:24][CH2:23][CH2:22][NH:21]1.[NH2:29][C:30]1[N:38]=[C:37]2[C:33]([N:34]=[CH:35][NH:36]2)=[C:32](Cl)[N:31]=1>C(O)CCC>[NH2:29][C:30]1[N:38]=[C:37]2[C:33]([N:34]=[CH:35][NH:36]2)=[C:32]([N:21]2[CH2:22][CH2:23][CH2:24][C@@H:20]2[CH2:19][O:18][C:17]2[CH:25]=[CH:26][CH:27]=[CH:28][C:16]=2[Cl:15])[N:31]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67315041HCID 67315041, compoundHCID 1785084356-chloro-1H-purin-2-amine

Product 1

HCID 178508579HCID 178508579, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

7.1 93.84 μl of triethylamine are added dropwise to a mixture of 75 mg of (R)-2-(2-chlorophenoxymethyl)pyrrolidine trifluoroacetate and 39.5 mg of 2-amino-6-chloro-9H-purine in 1 ml of n-butanol. The reaction mixture is stirred at 100° for 2.5 hours. The mixture is cooled, the deposited precipitate is separated off, and the filtrate is chromatographed directly on a 12 g RP18 column. The isolated product fractions are subjected to conventional purification, giving 45.4 mg of 2-amino-6-[(R)-2-(2-chlorophenoxymethyl)-pyrrolidin-1-yl]-9H-purine (“A36”); HPLC retention time 2.77 minutes; gradient P2; [M+H]+ 345.

Workup

  1. temperatureThe mixture is cooled
  2. customthe deposited precipitate is separated off
  3. customthe filtrate is chromatographed directly on a 12 g RP18 column
  4. customThe isolated product fractions are subjected to conventional purification

Sources & evidence

ORD record
ord-ff78be6ca0844680a82bcbaa7a5263a8
Source dataset
uspto-grants-2011_07
Patent number
US07977343B2

Reaction notes

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