Methanesulfonamide → HCID 46947711, compound

HRID 2047069Notes

Reaction equation

HRID 2047069 reaction equation
C[Si](C)(C)CCOC[N:7](COCC[Si](C)(C)C)[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]4[C:25]([CH:26]=3)=[CH:24][CH:23]=[CH:22][CH:21]=4)=[C:12]2[N:11]=[C:10]([CH:27]2[CH2:32][CH2:31][CH:30]([CH2:33][C:34](O)=[O:35])[CH2:29][CH2:28]2)[C:9]=1[Br:37].[CH3:48][S:49]([NH2:52])(=[O:51])=[O:50].Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.ClCCl>[NH2:7][C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]4[C:25]([CH:26]=3)=[CH:24][CH:23]=[CH:22][CH:21]=4)=[C:12]2[N:11]=[C:10]([CH:27]2[CH2:32][CH2:31][CH:30]([CH2:33][C:34]([NH:52][S:49]([CH3:48])(=[O:51])=[O:50])=[O:35])[CH2:29][CH2:28]2)[C:9]=1[Br:37]

Participants

6

Reactant 3

HCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67494550HCID 67494550, compound

Product 1

HCID 46947711HCID 46947711, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-bromo-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetic acid (60 mg, 0.081 mmol), methanesulfonamide (12 mg, 0.122 mmol), 4-dimethylaminopyridine (20 mg, 0.163 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (32 mg, 0.163 mmol) in dichloromethane (2.0 ml) was stirred at room temperature for 16 h. The reaction mixture was concentrated in vacuo. The crude mixture was dissolved in methanol (2 ml) and treated with 1N hydrochloride solution (2 ml) at 65° C. for 2 h. The reaction solution was concentrated and purified by prep-LC to afford the title compound (two isomers, cis and trans). Isomer 1: LC/MS RT=3.63 min. Mass calculated for, M+H 557.09, observed 557.09. Isomer 2: LC/MS RT=3.88 min. Mass calculated for, M+H 557.09, observed 557.09.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionThe crude mixture was dissolved in methanol (2 ml)
  3. additiontreated with 1N hydrochloride solution (2 ml) at 65° C. for 2 h
  4. concentrationThe reaction solution was concentrated
  5. custompurified by prep-LC

Sources & evidence

ORD record
ord-c2048afb6bf64131a6d21d5b65b84912
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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