Diisopropylethylamine → HCID 59743422, compound

HRID 1947032Notes

Reaction equation

[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([N:8]([CH3:13])[S:9]([CH3:12])(=[O:11])=[O:10])[CH2:4][CH2:3]1.CCN(C(C)C)C(C)C.CS([C:26]1[N:31]=[C:30]([N:32]2[C:40]3[C:35](=[C:36]([CH2:41][N:42]([CH2:44][CH2:45][O:46][CH3:47])[CH3:43])[CH:37]=[CH:38][CH:39]=3)[CH:34]=[CH:33]2)[CH:29]=[CH:28][N:27]=1)=O>CN1C(=O)CCC1>[CH3:47][O:46][CH2:45][CH2:44][N:42]([CH2:41][C:36]1[CH:37]=[CH:38][CH:39]=[C:40]2[C:35]=1[CH:34]=[CH:33][N:32]2[C:30]1[CH:29]=[CH:28][N:27]=[C:26]([NH:1][CH:2]2[CH2:7][CH2:6][CH:5]([N:8]([CH3:13])[S:9]([CH3:12])(=[O:11])=[O:10])[CH2:4][CH2:3]2)[N:31]=1)[CH3:43]

Participants

Conditions

Temperature: 130 °C

Procedure

N-(4-amino-cyclohexyl)-N-methyl-methanesulfonamide (567 mg, 2.12 mmol) and DIEA (0.44 mL) were stirred in NMP (0.7 mL) at RT for 1 h. [1-(2-Methanesulfinyl-pyrimidin-4-yl)-1H-indol-4-ylmethyl]-(2-methoxyethyl)-methyl-amine (305 mg, 0.85 mmol) in NMP (0.8 mL) was added, and the tube sealed and heated to 130° C. for 1 h. The mixture was then cooled to RT, decanted into water, stirred at RT overnight, and the filtrate filtered off and dried in vacuo, dissolved in DCM/ether, the precipitate filtered off, and the residue concentrated and crystallized from DCM/ether to yield N-{4-[4-(4-{[(2-methoxy-ethyl)-methyl-amino]-methyl}-indol-1-yl)-pyrimidin-2-ylamino]-cyclohexyl}-N-methyl-methanesulfonamide (Compound 203).

Workup

additionwas added
customthe tube sealed
temperatureThe mixture was then cooled to RT
customdecanted into water
filtrationthe filtrate filtered off
customdried in vacuo
dissolutiondissolved in DCM/ether
filtrationthe precipitate filtered off
concentrationthe residue concentrated
customcrystallized from DCM/ether

Sources & evidence

ORD record: ord-2536c5477e344e3c9f5863633c8b02b7
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399462B2

Reaction notes

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