Ammonium Chloride → HCID 57504290, compound

HRID 1097981Notes

Reaction equation

HRID 1097981 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]([OH:23])=O)=[C:11]2[CH:10]=[N:9]1.[Cl-].[NH4+].CC[N:38](C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C1COCC1.O>[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]([NH2:38])=[O:23])[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

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 57504289HCID 57504289, compound

Product 1

HCID 57504290HCID 57504290, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 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), ammonium chloride (3.0 mg, 0.054 mmol), DIPEA (7.0 mg, 0.054 mmol) and TBTU (7.0 mg, 0.021 mmol) in THF (1 mL) was stirred at ambient temperature for 3 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 9.18 (br s, 1H), 8.59 (s, 1H), 8.42 (s, 1H), 8.16 (d, 1H), 8.09 (s, 1H), 7.64 (m, 1H), 7.53 (m, 4H), 5.94 (s, 1H), 5.75 (br s, 1H), 5.57 (br s, 1H), 2.58 (m, 4H), 2.32 (s, 3H), HRMS: calcd for (M+H+) C22H2135ClN7O3: 466.1394. Found: 467.1426.

Workup

  1. customthe reaction mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-f4ffcafafa6f47ceacdbd9957f3882c8
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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