Triethylamine → 2-(4-(6-(5-Chloro-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidin-2-ylamino)-4-methylpyridin-3-yl)piperidin-1-yl)acetamide

HRID 2093820Notes

Reaction equation

HRID 2093820 reaction equation
[Cl:1][C:2]1[C:3]([NH:22][C:23]2[CH:27]=[C:26]([CH3:28])[NH:25][N:24]=2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[C:13]([CH3:15])[C:12]([CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[CH:11][N:10]=2)=[N:6][CH:7]=1.C(N(CC)CC)C.Br[CH2:37][C:38]([NH2:40])=[O:39]>CN(C=O)C>[Cl:1][C:2]1[C:3]([NH:22][C:23]2[CH:27]=[C:26]([CH3:28])[NH:25][N:24]=2)=[N:4][C:5]([NH:8][C:9]2[N:10]=[CH:11][C:12]([CH:16]3[CH2:17][CH2:18][N:19]([CH2:37][C:38]([NH2:40])=[O:39])[CH2:20][CH2:21]3)=[C:13]([CH3:15])[CH:14]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 696322-BromoacetamideHCID 671691565-chloro-N4-(5-methyl-1H-pyrazol-3-yl)-N2-(4-methyl-5-(piperidin-4-yl)pyridin-2-yl)pyrimidine-2,4-diamine

Product 1

HCID 582571302-(4-(6-(5-Chloro-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidin-2-ylamino)-4-methylpyridin-3-yl)piperidin-1-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-chloro-N4-(5-methyl-1H-pyrazol-3-yl)-N2-(4-methyl-5-(piperidin-4-yl)pyridin-2-yl)pyrimidine-2,4-diamine (50 mg, 0.12 mmol) and triethylamine (50 uL, 0.36 mmol) in DMF (1.5 mL), was added 2-bromo-acetamide (25 mg, 0.18 mmol). The mixture was stirred at room temperature for 2 hours. The reaction was filtered and the filtrate was purified by RP-HPLC to afford 2-(4-(6-(5-Chloro-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidin-2-ylamino)-4-methylpyridin-3-yl)piperidin-1-yl)acetamide as a white solid; 1H NMR (400 MHz, MeOD-d4) δ 8.30 (s, 1H), 8.21 (s, 1H), 7.28 (s, 1H), 6.19 (s, 1H), 4.0 (s, 2H), 3.80-3.73 (m, 2H), 3.33-3.21 (m, 3H), 2.61 (s, 3H), 2.37 (s, 3H), 2.37-2.32 (m, 2H), 2.20-2.16 (m, 2H); ESMS m/z 456.2 (M+H+).

Workup

  1. filtrationThe reaction was filtered
  2. customthe filtrate was purified by RP-HPLC

Sources & evidence

ORD record
ord-e943fc50bc4e49d29d95f62b0aadaf22
Source dataset
uspto-grants-2013_05
Patent number
US08445505B2

Reaction notes

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