Methanesulfonyl chloride → Hydrochloric Acid

HRID 1050527Notes

Reaction equation

HRID 1050527 reaction equation
[CH3:1][O:2][C:3]1[CH:39]=[CH:38][C:6]([C:7]([NH:9][C@@H:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]3[N:17]=[C:18]([NH:25][C:26]4[CH:31]=[CH:30][C:29]([CH:32]5[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]5)=[CH:28][CH:27]=4)[C:19]([C:22]([NH2:24])=[O:23])=[N:20][CH:21]=3)[CH2:11]2)=[O:8])=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.[CH3:49][S:50]([Cl:53])(=[O:52])=[O:51]>CN1C(=O)CCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][C@@H:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]3[N:17]=[C:18]([NH:25][C:26]4[CH:31]=[CH:30][C:29]([CH:32]5[CH2:37][CH2:36][N:35]([S:50]([CH3:49])(=[O:52])=[O:51])[CH2:34][CH2:33]5)=[CH:28][CH:27]=4)[C:19]([C:22]([NH2:24])=[O:23])=[N:20][CH:21]=3)[CH2:11]2)=[O:8])=[CH:38][CH:39]=1.[ClH:53]

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 118133410HCID 118133410, compound

Product 2

HCID 313Hydrochloric AcidHCID 118114457HCID 118114457, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Compound 163 (32 mg, 0.056 mmol) was dissolved in 3 mL NMP. To it were added DIEA (60 μL, 0.34 mmol) and then methanesulfonyl chloride (13 μL, 0.17 mmol). The reaction was quenched in 20 m using TFA (0.1 mL). The mixture was directly subjected to reverse phase preparative HPLC to isolate (R)-5-(3-(4-methoxybenzamido)piperidin-1-yl)-3-(4-(1-(methylsulfonyl)piperidin-4-yl)phenylamino)pyrazine-2-carboxamide (173) as HCl salt. MS found for C30H37N7O5S as (M+H)+ 608.2, (M−H)− 606.3. UV: λ=304, 335, 372 nm.

Workup

  1. customThe reaction was quenched in 20 m

Sources & evidence

ORD record
ord-4a63caf73d8041d38c4581e31d73d20c
Source dataset
uspto-grants-2016_07
Patent number
US09382246B2

Reaction notes

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