Aniline → HCID 67998382, compound

HRID 1969664Notes

Reaction equation

HRID 1969664 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8](=O)([O:39]C1C=CC([N+]([O-])=O)=CC=1)[O:9][C@@H:10]1[CH2:14][C@H:13]([C:15]2[N:19]3[C:20]4[CH:26]=[CH:25][N:24]([S:27]([C:30]5[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=5)(=[O:29])=[O:28])[C:21]=4[N:22]=[CH:23][C:18]3=[N:17][N:16]=2)[C@H:12]([CH2:37][CH3:38])[CH2:11]1>CN(C1C=CN=CC=1)C.O1CCOCC1>[C:2]1([NH:1][C:8](=[O:39])[O:9][C@@H:10]2[CH2:14][C@H:13]([C:15]3[N:19]4[C:20]5[CH:26]=[CH:25][N:24]([S:27]([C:30]6[CH:31]=[CH:32][C:33]([CH3:34])=[CH:35][CH:36]=6)(=[O:29])=[O:28])[C:21]=5[N:22]=[CH:23][C:18]4=[N:17][N:16]=3)[C@H:12]([CH2:37][CH3:38])[CH2:11]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6115AnilineHCID 58558041HCID 58558041, compound

Product 1

HCID 67998382HCID 67998382, compoundYield 63.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 312751,4-DioxaneSolvent2×

Procedure

To aniline (0.063 g, 0.677 mmol) and DMAP (0.033 g, 0.271 mmol) in 1,4-dioxane (1 mL) at about 40° C. was added a solution of (1S,3R,4S)-3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl 4-nitrophenyl carbonate (0.080 g, 0.135 mmol, prepared from Example #42 Step N) in 1,4-dioxane (1 mL). After about 2 h, the solvent was removed and the residue was purified by silica gel chromatography (12 g) eluting with 0-40% EtOAc in DCM to give (1S,3R,4S)-3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl phenylcarbamate (0.0468 g, 63%): LC/MS (Table 1, Method b) Rt=2.58 min; MS m/z: 545 (M+H)+.

Workup

  1. customthe solvent was removed
  2. customthe residue was purified by silica gel chromatography (12 g)
  3. washeluting with 0-40% EtOAc in DCM

Sources & evidence

ORD record
ord-68bb69e9768247b1b7d1fbcc98c82ddf
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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