Water → HCID 57504291, compound

HRID 1097982Notes

Reaction equation

HRID 1097982 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]2=[N:13][CH:14]=[N:15][C:16]([O:17][CH:18]([C:24]([NH:26][C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][N:28]=3)=[O:25])[CH2:19][CH2:20][C:21](O)=[O:22])=[C:11]2[CH:10]=[N:9]1.CN.[CH3:36][N:37](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.O>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]2=[N:13][CH:14]=[N:15][C:16]([O:17][CH:18]([CH2:19][CH2:20][C:21]([NH:37][CH3:36])=[O:22])[C:24]([NH:26][C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][N:28]=3)=[O:25])=[C:11]2[CH:10]=[N:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 6329MethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 575042894-{[1-(2-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]oxy}-5-[(5-methylpyridin-2-yl)amino]-5-oxopentanoic acid

Product 1

HCID 57504291HCID 57504291, compoundYield 56.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-{[1-(2-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]oxy}-5-[(5-methylpyridin-2-yl)amino]-5-oxopentanoic acid (5.0 mg, 0.011 mmol), methylamine (0.021 ml (2M in THF), 0.043 mmol) and TBTU (7.0 mg, 0.021 mmol) in THF (1 mL) was stirred at ambient temperature for 5 hrs. Water (1 mL) was added and the reaction mixture was purified by preparative HPLC: Mobile phase A: 100% ACN, Mobile phase B: 5% ACN+95% 0.1M NH4OAc in water; Gradient: 0% A to 50% A over 45 min; Flow: 25 ml/min; UV: 235 nm, to give the title compound (3.0 mg). 1H NMR (500 MHz, CDCl3) δ 8.88 (br s, 1H), 8.57 (s, 1H), 8.39 (s, 1H), 8.11 (m, 2H), 7.62 (m, 1H), 7.51 (m, 4H), 5.91 (m, 1H), 5.63 (br s, 1H), 2.82 (d, 3H), 2.51 (m, 4H), 2.30 (s, 3H), HRMS: calcd for (M+H+) C23H2335ClN7O3: 480.1551. Found: 480.1503.

Workup

  1. customthe reaction mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-a4ca3a8346694c439b524e18fea99dc3
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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