Diethylamine → HCID 178464182, compound

HRID 2388959Notes

Reaction equation

HRID 2388959 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[C:13]3[C:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[O:26][CH3:27])=[N:18][NH:17][C:14]3=[N:15][CH:16]=2)=[CH:7][C:3]=1[C:4]([OH:6])=O.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:39]2[N:40]=[CH:41][CH:42]=C[C:38]=2N=N1.C(N(C(C)C)CC)(C)C.C(NCC)C.C(=O)(O)[O-].[Na+]>CN(C=O)C.ClCCl>[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[C:13]3[C:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[O:26][CH3:27])=[N:18][NH:17][C:14]3=[N:15][CH:16]=2)=[CH:7][C:3]=1[C:4]([N:40]([CH2:41][CH3:42])[CH2:39][CH3:38])=[O:6]

Participants

8

Reactant 5

HCID 8021DiethylamineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178489398HCID 178489398, compound

Product 1

HCID 178464182HCID 178464182, compoundYield 7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

40 mg (0.11 mmol) of 2-amino-5-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-benzoic acid and 63 mg (0.16 mmol) of O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate were dissolved in 2 mL of DMF. 40 μL (30 mg, 0.23 mmol) of di-iso-propyl ethyl amine and 100 μL (70 mg, 0.96 mmol) of diethylamine were added and the resulting mixture irradiated in a Personal Chemistry® Optimizer to 130° C. for 30 min. The resulting mixture was distributed between a saturated aqueous solution of sodium bicarbonate and dichloromethane and the organic phase was dried over sodium sulfate and evaporated. The resulting crude was purified by mass-triggered reverse-phase HPLC to afford 3.2 mg (7.7 μmol, 7%) of 2-amino-N,N-diethyl-5-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-benzamide as an off-white solid. 1H NMR (500 MHz, DMSO-d6) δ 13.72 (s, br., 1H), 8.75 (d, 1H), 8.17 (d, 1H), 7.64 (dd, 1H), 7.49 (dd, 1H), 7.46 (ddd, 1H), 7.32 (d, 1H), 7.21 (d(d), 1H), 7.09 (ddd, 1H), 6.85 (d, 1H), 3.84 (s, 3H), 3.4-3.3 (m, 4H), 1.15-1.05 (m, br., 6H), MS: m/z 416.1 (M+H+).

Workup

  1. customthe resulting mixture irradiated in a Personal Chemistry® Optimizer to 130° C. for 30 min
  2. dry with materialthe organic phase was dried over sodium sulfate
  3. customevaporated
  4. customThe resulting crude was purified by mass-triggered reverse-phase HPLC

Sources & evidence

ORD record
ord-88a3848aacce4eda8cf120d45d9b420f
Source dataset
uspto-grants-2012_09
Patent number
US08268994B2

Reaction notes

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