Dimethylamine → HCID 71508937, compound

HRID 1499729Notes

Reaction equation

HRID 1499729 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:19]([C:21]3[C:22]([O:38][CH3:39])=[C:23]([C:29]4[CH:34]=[CH:33][N:32]=[C:31]([C:35]([OH:37])=O)[CH:30]=4)[C:24]([CH3:28])=[C:25]([Cl:27])[CH:26]=3)[CH3:20])[N:17]=[CH:18][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:19]([C:21]3[C:22]([O:38][CH3:39])=[C:23]([C:29]4[CH:34]=[CH:33][N:32]=[C:31]([C:35]([N:2]([CH3:3])[CH3:1])=[O:37])[CH:30]=4)[C:24]([CH3:28])=[C:25]([Cl:27])[CH:26]=3)[CH3:20])[N:17]=[CH:18][C:11]=12

Participants

7

Reactant 5

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 86677664HCID 86677664, compound

Product 1

HCID 71508937HCID 71508937, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dimethylamine (2.0 M) in THF (0.14 mL, 0.28 mmol) was added to a solution of 4-{3-[1-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl}pyridine-2-carboxylic acid (18.6 mg, 0.042 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 the addition of triethylamine (8.8 μL, 0.064 mmol). The reaction was stirred for 1 hour, then quenched with water. The mixture was purified on 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 C23H25ClN7O2 (M+H)+: m/z=466.2; Found: 466.2.

Workup

  1. customquenched with water
  2. customThe mixture was purified on RP-HPLC (XBridge C18 column
  3. washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min)

Sources & evidence

ORD record
ord-2dd476888a584469a8ae497c6f279f1a
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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