Propionyl chloride → Hydrochloric Acid

HRID 1050525Notes

Reaction equation

HRID 1050525 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.[C:49]([Cl:53])(=[O:52])[CH2:50][CH3:51]>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]([C:49](=[O:52])[CH2:50][CH3:51])[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 62324Propionyl chlorideHCID 81531DiisopropylethylamineHCID 118133410HCID 118133410, compound

Product 2

HCID 313Hydrochloric AcidHCID 118115206HCID 118115206, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Compound 163 (50 mg, 0.085 mmol) was dissolved in 3 mL NMP. To it were added DIEA (74 μL, 0.425 mmol) and then propionyl chloride (23 mg, 0.255 mmol). The reaction was quenched in 10 m using TFA (0.2 mL). The mixture was directly subjected to reverse phase preparative HPLC to isolate (R)-5-(3-(4-methoxybenzamido)piperidin-1-yl)-3-(4-(1-propionylpiperidin-4-yl)phenylamino)pyrazine-2-carboxamide (170) as HCl salt. MS found for C32H39N7O4 as (M+H)+ 586.2, (M−H)− 584.4. UV: λ=257, 279, 304, 335, 372 nm.

Workup

  1. customThe reaction was quenched in 10 m

Sources & evidence

ORD record
ord-26821493cebf4f59a83b7493d0866023
Source dataset
uspto-grants-2016_07
Patent number
US09382246B2

Reaction notes

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