2,6-Dimethylmorpholine, cis- → 2-{[(2R,6S)-2,6-Dimethyl-4-morpholinyl]methyl}-N-{1-(phenylsulfonyl)-6-[1-(phenylsulfonyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-1H-indazol-4-yl}-1,3-thiazole-4-carboxamide

HRID 244711Notes

Reaction equation

HRID 244711 reaction equation
Cl[CH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8]([NH:10][C:11]2[CH:19]=[C:18]([C:20]3[CH:21]=[C:22]4[CH:28]=[N:27][N:26]([S:29]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)(=[O:31])=[O:30])[C:23]4=[N:24][CH:25]=3)[CH:17]=[C:16]3[C:12]=2[CH:13]=[N:14][N:15]3[S:38]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)(=[O:40])=[O:39])=[O:9])[N:7]=1.[CH3:47][C@H:48]1[O:53][C@@H:52]([CH3:54])[CH2:51][NH:50][CH2:49]1>>[CH3:54][C@H:52]1[O:53][C@@H:48]([CH3:47])[CH2:49][N:50]([CH2:2][C:3]2[S:4][CH:5]=[C:6]([C:8]([NH:10][C:11]3[CH:19]=[C:18]([C:20]4[CH:21]=[C:22]5[CH:28]=[N:27][N:26]([S:29]([C:32]6[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=6)(=[O:31])=[O:30])[C:23]5=[N:24][CH:25]=4)[CH:17]=[C:16]4[C:12]=3[CH:13]=[N:14][N:15]4[S:38]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)(=[O:40])=[O:39])=[O:9])[N:7]=2)[CH2:51]1

Participants

3

Reactant 2

HCID 6415002,6-Dimethylmorpholine, cis-2×HCID 583563662-(Chloromethyl)-N-{1-(phenylsulfonyl)-6-[1-(phenylsulfonyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-1H-indazol-4-yl}-1,3-thiazole-4-carboxamide

Product 1

HCID 583564282-{[(2R,6S)-2,6-Dimethyl-4-morpholinyl]methyl}-N-{1-(phenylsulfonyl)-6-[1-(phenylsulfonyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-1H-indazol-4-yl}-1,3-thiazole-4-carboxamideYield 167.2%

Conditions

Temperature
90 °C

Procedure

2-(Chloromethyl)-N-{1-(phenylsulfonyl)-6-[1-(phenylsulfonyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-1H-indazol-4-yl}-1,3-thiazole-4-carboxamide (53 mg, 0.077 mmol) and (2R,6S)-2,6-dimethylmorpholine (0.5 ml, 0.077 mmol) were placed in a microwave vial and heated in a microwave at 90° C. for 15 min, allowed to cool, then heated again in the microwave at 90° C. for 15 min. A further portion of (2R,6S)-2,6-dimethylmorpholine (0.3 ml) was added and the mixture was heated in the microwave at 90° C. for 30 mins. Volatiles were removed under a stream of nitrogen to give the title compound as a pale yellow solid (99 mg). The material was used without further purification.

Workup

  1. temperatureto cool
  2. temperatureheated again in the microwave at 90° C. for 15 min
  3. temperaturethe mixture was heated in the microwave at 90° C. for 30 mins
  4. customVolatiles were removed under a stream of nitrogen

Sources & evidence

ORD record
ord-ad8c08a3a58047d0a2829146f8d6fe00
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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