Triethylamine → HCID 178434477, compound

HRID 2046979Notes

Reaction equation

C(OC1C=C(C2CCNCC2)C(C)=CC=1[NH:18][C:19]1[N:24]=[C:23]2[NH:25][N:26]=[C:27]([CH3:28])[C:22]2=[C:21]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[S:36]([CH:39]([CH3:41])[CH3:40])(=[O:38])=[O:37])[N:20]=1)(C)C.BrCCOC.C(N(CC)CC)C>>[CH:39]([S:36]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[NH:29][C:21]1[N:20]=[C:19]([NH2:18])[N:24]=[C:23]2[NH:25][N:26]=[C:27]([CH3:28])[C:22]=12)(=[O:37])=[O:38])([CH3:41])[CH3:40]

Participants

Reactant 3

HCID 8471Triethylamine

HCID 809722-Bromoethyl methyl ether

HCID 178428323HCID 178428323, compound

Product 1

HCID 178434477HCID 178434477, compound

Conditions

Temperature: 100 °C

Procedure

The mixture of N6-(2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl)-N4-(2-(isopropylsulfonyl)phenyl)-3-methyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine (26.6 mg, 0.046 mmol), 1-bromo-2-methoxyethane (1.0 N in DMF, 0.46 mmol, 0.46 mL), and triethylamine (1.0 N in DMF, 0.46 mmol, 0.46 mL) was heated at 100° C. for 10 min The resulting reaction mixture was purified by RP-HPLC to afford N6-(2-isopropoxy-4-(1-methoxyethyl)piperidin-4-yl)-5-methylphenyl)-N4-(2-(isopropylsulfonyl)phenyl)-3-methyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine. MS (ES+): 636.3 (MH+).

Workup

customThe resulting reaction mixture
customwas purified by RP-HPLC

Sources & evidence

ORD record: ord-25c8f76ed0644c269b2f41064225dccc
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592432B2

Reaction notes

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