Dimethylamine → 4-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]-N,N-dimethylpyridine-2-carboxamide

HRID 1499700Notes

Reaction equation

HRID 1499700 reaction equation
[CH3:1][NH:2][CH3:3].C1COCC1.[NH2:9][C:10]1[N:15]=[CH:14][N:13]=[C:12]2[N:16]([CH:20]([C:22]3[C:23]([O:39][CH3:40])=[C:24]([C:30]4[CH:35]=[CH:34][N:33]=[C:32]([C:36](O)=[O:37])[CH:31]=4)[C:25]([CH3:29])=[C:26]([Cl:28])[CH:27]=3)[CH3:21])[N:17]=[C:18]([CH3:19])[C:11]=12.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O>[NH2:9][C:10]1[N:15]=[CH:14][N:13]=[C:12]2[N:16]([CH:20]([C:22]3[C:23]([O:39][CH3:40])=[C:24]([C:30]4[CH:35]=[CH:34][N:33]=[C:32]([C:36]([N:2]([CH3:3])[CH3:1])=[O:37])[CH:31]=4)[C:25]([CH3:29])=[C:26]([Cl:28])[CH:27]=3)[CH3:21])[N:17]=[C:18]([CH3:19])[C:11]=12

Participants

7

Reactant 5

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 866776434-{3-[1-(4-Amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl}pyridine-2-carboxylic acid

Product 1

HCID 715107654-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]-N,N-dimethylpyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.0 M Dimethylamine in THF (0.14 mL, 0.28 mmol) was added to a solution of 4-{3-[1-(4-amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl}pyridine-2-carboxylic acid (9.6 mg, 0.021 mmol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (10 mg, 0.03 mmol) in N,N-dimethylformamide (0.7 mL) at room temperature followed by addition of triethylamine (8.8 μL, 0.064 mmol). The reaction was stirred for 1 hour. The crude mixture was purified using RP-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min) to give the desired product. The product was isolated as a racemic mixture. LCMS calculated for C24H27ClN7O2 (M+H)+: m/z=480.2; Found: 480.2.

Workup

  1. customThe crude mixture was purified
  2. washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min)

Sources & evidence

ORD record
ord-5ea4f0478dd148a3b9941a3ee890d7b5
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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