Triethylamine → HCID 178485765, compound

HRID 2046977Notes

Reaction equation

[CH:1]([O:4][C:5]1[CH:10]=[C:9]([CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[C:8]([CH3:17])=[CH:7][C:6]=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)([CH3:3])[CH3:2].Br[CH2:43][C:44]([NH2:46])=[O:45].[CH2:47](N(CC)CC)C>>[CH:1]([O:4][C:5]1[C:6]([NH:18][C:19]2[N:24]=[C:23]3[NH:25][N:26]=[C:27]([CH3:28])[C:22]3=[C:21]([NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[S:36]([CH:39]([CH3:41])[CH3:40])(=[O:38])=[O:37])[N:20]=2)=[CH:7][C:8]([CH3:17])=[C:9]([CH:11]2[CH2:16][CH2:15][N:14]([CH2:43][C:44]([NH:46][CH3:47])=[O:45])[CH2:13][CH2:12]2)[CH:10]=1)([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 8471Triethylamine

HCID 696322-Bromoacetamide

HCID 178428323HCID 178428323, compound

Product 1

HCID 178485765HCID 178485765, 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 (20 mg, 0.035 mmol), 2-bromoacetamide (0.1 N in DMF, 0.070 mmol, 0.70 mL) and triethylamine (1.0 N in DMF, 0.105 mmol, 0.105 mL) was heated at 100° C. for 10 min. The resulting reaction mixture was purified by RP-HPLC to afford 2-(4-(5-isopropoxy-4-(4-(2-(isopropylsulfonyl)phenylamino)-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)-2-methylphenyl)piperidin-1-yl)-N-methylacetamide. MS (ES+): 649.3 (MH+).

Workup

customThe resulting reaction mixture
customwas purified by RP-HPLC

Sources & evidence

ORD record: ord-d5c4f7fd008d4d0f984a3d5171ddc1d0
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592432B2

Reaction notes

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