Water → HCID 59743443, compound

HRID 1947031Notes

Reaction equation

CCN(C(C)C)C(C)C.[NH2:10][CH:11]1[CH2:16][CH2:15][CH:14]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH2:13][CH2:12]1.CS([C:25]1[N:30]=[C:29]([C:31]2[C:39]3[C:34](=[C:35]([O:40][CH2:41][CH2:42][CH2:43][S:44]([CH3:47])(=[O:46])=[O:45])[CH:36]=[CH:37][CH:38]=3)[NH:33][N:32]=2)[CH:28]=[CH:27][N:26]=1)=O.O>CN1C(=O)CCC1>[CH3:47][S:44]([CH2:43][CH2:42][CH2:41][O:40][C:35]1[CH:36]=[CH:37][CH:38]=[C:39]2[C:34]=1[NH:33][N:32]=[C:31]2[C:29]1[CH:28]=[CH:27][N:26]=[C:25]([NH:10][CH:11]2[CH2:16][CH2:15][CH:14]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH2:13][CH2:12]2)[N:30]=1)(=[O:46])=[O:45]

Participants

Conditions

Temperature: 130 °C

Procedure

DIEA (0.31 mL) and N-(4-aminocyclohexyl)-methanesulfonamide (348 mg) were stirred in NMP (1 mL) at RT for 1 hour. 3-(2-Methanesulfinyl-pyrimidin-4-yl)-7-(3-methane-sulfonyl-propoxy)-1H-indazole (200 mg, 0.5 mmol) was added to the mixture and stirred at 130° C. for 2.5 h. The reaction mixture was then poured into water and the precipitate purified on a silica column using flash chromatography, eluting with hexane:EtOAc:MeOH 5:4.5:0.5 to yield N-(-4-{4-[7-(3-methanesulfonyl-propoxy)-1H-indazol-3-yl]-pyrimidin-2-ylamino}-cyclo-hexyl)-methanesulfonamide (Compound 315).

Workup

customthe precipitate purified on a silica column
washeluting with hexane:EtOAc:MeOH 5:4.5:0.5

Sources & evidence

ORD record: ord-3e42e54fd6454d0e81a0bc7018393c26
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399462B2

Reaction notes

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