(2R)-1-oxo-1-(1-(phenylsulfonyl)-4-(tetrahydro-2H-pyran-3-ylamino)-1H-pyrrolo[2,3-b]pyridin-5-ylamino)propan-2-yl acetate → (1R)-1-(6-(phenylsulfonyl)-1-(tetrahydro-2H-pyran-3-yl)-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2-yl)ethyl acetate

HRID 1257660Notes

Reaction equation

HRID 1257660 reaction equation
[C:1]([O:4][C@H:5]([CH3:34])[C:6](=O)[NH:7][C:8]1[C:9]([NH:26][CH:27]2[CH2:32][CH2:31][CH2:30][O:29][CH2:28]2)=[C:10]2[CH:16]=[CH:15][N:14]([S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C:11]2=[N:12][CH:13]=1)(=[O:3])[CH3:2]>C(O)(=O)C>[C:1]([O:4][C@@H:5]([C:6]1[N:26]([CH:27]2[CH2:32][CH2:31][CH2:30][O:29][CH2:28]2)[C:9]2=[C:10]3[CH:16]=[CH:15][N:14]([S:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)(=[O:18])=[O:19])[C:11]3=[N:12][CH:13]=[C:8]2[N:7]=1)[CH3:34])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 67323050(2R)-1-oxo-1-(1-(phenylsulfonyl)-4-(tetrahydro-2H-pyran-3-ylamino)-1H-pyrrolo[2,3-b]pyridin-5-ylamino)propan-2-yl acetate

Product 1

HCID 67350442(1R)-1-(6-(phenylsulfonyl)-1-(tetrahydro-2H-pyran-3-yl)-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2-yl)ethyl acetateYield 66%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of (2R)-1-oxo-1-(1-(phenylsulfonyl)-4-(tetrahydro-2H-pyran-3-ylamino)-1H-pyrrolo[2,3-b]pyridin-5-ylamino)propan-2-yl acetate (830 mg, 1.7 mmol) in acetic acid (10 mL) was stirred at 105° C. for 5 h, then the reaction was cooled down and concentrated. Purification by flash chromatography (40 to 100% ethyl acetate in heptane) afforded 525 mg (66%) of (1R)-1-(6-(phenylsulfonyl)-1-(tetrahydro-2H-pyran-3-yl)-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2-yl)ethyl acetate. LCMS (Method E, ESI): RT=1.49 min, m+H=469.2; 1H NMR (400 MHz, CDCl3) δ 8.25-7.99 (m, 2H), 7.84 (s, 1H), 7.61-7.35 (m, 4H), 6.58 (d, J=4.2 Hz, 1H), 5.04 (t, J=12.8 Hz, 1H), 4.02-3.82 (m, 2H), 3.80-3.55 (m, 2H), 3.47 (dd, J=11.1, 6.1 Hz, 1H), 2.86 (s, 2H), 2.11-1.93 (m, 1H), 2.17 (s, 3H), 1.80 (dtd, J=14.6, 7.2, 3.7 Hz, 1H), 1.74-1.51 (m, 3H).

Workup

  1. temperaturethe reaction was cooled down
  2. concentrationconcentrated
  3. customPurification by flash chromatography (40 to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-51771bd34bd94d539993e58185e3b6a2
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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