Hydrochloric Acid → 4-(7-Amino-6-bromo-3-quinolin-3-yl-pyrazolo[1,5-a]pyrimidin-5-yl)-cyclohexanecarboxylic acid

HRID 2047021Notes

Reaction equation

HRID 2047021 reaction equation
C[O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[C:16]([Br:17])=[C:15]([N:18](COCC[Si](C)(C)C)COCC[Si](C)(C)C)[N:14]3[N:35]=[CH:36][C:37]([C:38]4[CH:39]=[N:40][C:41]5[C:46]([CH:47]=4)=[CH:45][CH:44]=[CH:43][CH:42]=5)=[C:13]3[N:12]=2)[CH2:7][CH2:6]1)=[O:4].CO.[OH-].[Na+].Cl>O>[NH2:18][C:15]1[N:14]2[N:35]=[CH:36][C:37]([C:38]3[CH:39]=[N:40][C:41]4[C:46]([CH:47]=3)=[CH:45][CH:44]=[CH:43][CH:42]=4)=[C:13]2[N:12]=[C:11]([CH:8]2[CH2:7][CH2:6][CH:5]([C:3]([OH:4])=[O:2])[CH2:10][CH2:9]2)[C:16]=1[Br:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 66738157HCID 66738157, compound

Product 1

HCID 581734464-(7-Amino-6-bromo-3-quinolin-3-yl-pyrazolo[1,5-a]pyrimidin-5-yl)-cyclohexanecarboxylic acidYield 34.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-{7-[Bis-(2-trimethylsilanyl-ethoxymethyl)-amino]-6-bromo-3-quinolin-3-yl-pyrazolo[1,5-a]pyrimidin-5-yl}-cyclohexanecarboxylic acid methyl ester (100 mg, 0.135 mmol) in 2:1 MeOH:H2O (3 mL) was treated with 2N NaOH(aq) (0.5 mL). The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was treated with 1N hydrochloride solution (2 ml) at 65° C. for 4 h. The reaction mixture was concentrated and purified by prep-LC to afford the title compound (21.8 mg): LC/MS RT=3.57 min. Mass calculated for, M+H 466.08, observed 466.08.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by prep-LC

Sources & evidence

ORD record
ord-df32b7aa205a4084b73565ef474cd4e1
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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