4-Methylmorpholine → 1-[9-((1R,2S,3R,4S)-2,3-Dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-1H-pyrazole-4-carboxylic acid (pyridin-2-ylmethyl)-amide

HRID 2382494Notes

Reaction equation

HRID 2382494 reaction equation
[OH:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([NH:8][C:9](=[O:12])[CH2:10][CH3:11])[CH2:4][C@H:3]1[N:13]1[CH:21]=[N:20][C:19]2[C:14]1=[N:15][C:16]([N:37]1[CH:41]=[C:40]([C:42]([OH:44])=O)[CH:39]=[N:38]1)=[N:17][C:18]=2[NH:22][CH2:23][CH:24]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[NH2:45][CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][N:48]=1.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[N:48]1[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=1[CH2:46][NH:45][C:42]([C:40]1[CH:39]=[N:38][N:37]([C:16]2[N:15]=[C:14]3[C:19]([N:20]=[CH:21][N:13]3[C@@H:3]3[CH2:4][C@H:5]([NH:8][C:9](=[O:12])[CH2:10][CH3:11])[C@@H:6]([OH:7])[C@H:2]3[OH:1])=[C:18]([NH:22][CH2:23][CH:24]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[N:17]=2)[CH:41]=1)=[O:44]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 195092-PyridinemethanamineHCID 757711-HydroxybenzotriazoleHCID 666310391-[9-((1R,2S,3R,4S)-2,3-Dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-1H-pyrazole-4-carboxylic acid

Product 1

HCID 666304691-[9-((1R,2S,3R,4S)-2,3-Dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-1H-pyrazole-4-carboxylic acid (pyridin-2-ylmethyl)-amide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture comprising 1-[9-((1R,2S,3R,4S)-2,3-dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-1H-pyrazole-4-carboxylic acid (0.06 g, 0.01 mmol) in dry DCM (10 ml) is treated with 2-aminomethylpyridine (0.021 g, 0.2 mmol) followed by HOBt (0.027 g, 0.2 mmol), 1-[Bis(dimethylamino)methylene]-1H-benzotriazoliumhexafluorophosphate-3-oxide HBTU (0.076 g, 0.2 mmol), N-methyl morpholine (0.02 g, 0.2 mmol) and DMAP (1 ml). The resulting mixture is stirred at room temperature for 24 h and then concentrated in vacuo. The resulting residue purified by preparative TLC eluting with 10% MeOH in chloroform to afford the title compound. (MH+ 687.1)

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resulting residue purified by preparative TLC
  3. washeluting with 10% MeOH in chloroform

Sources & evidence

ORD record
ord-e81b8cdfc42e4aa595ad7f57fa122e14
Source dataset
uspto-grants-2012_09
Patent number
US08258141B2

Reaction notes

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