Triethylamine → HCID 71280663, compound

HRID 1497923Notes

Reaction equation

HRID 1497923 reaction equation
[F:1][C:2]1([F:36])[CH2:5][CH:4]([C:6]2[O:10][N:9]=[C:8]([C:11]3[CH:12]=[CH:13][C:14]([CH3:35])=[C:15]([NH:17][C:18]([C:20]4[N:24]5[CH:25]=[CH:26][C:27]([CH:29]6[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]6)=[CH:28][C:23]5=[N:22][CH:21]=4)=[O:19])[CH:16]=3)[N:7]=2)[CH2:3]1.CCN(CC)CC.[CH3:44][S:45](Cl)(=[O:47])=[O:46]>ClCCl>[F:36][C:2]1([F:1])[CH2:5][CH:4]([C:6]2[O:10][N:9]=[C:8]([C:11]3[CH:12]=[CH:13][C:14]([CH3:35])=[C:15]([NH:17][C:18]([C:20]4[N:24]5[CH:25]=[CH:26][C:27]([CH:29]6[CH2:34][CH2:33][N:32]([S:45]([CH3:44])(=[O:47])=[O:46])[CH2:31][CH2:30]6)=[CH:28][C:23]5=[N:22][CH:21]=4)=[O:19])[CH:16]=3)[N:7]=2)[CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 71280734HCID 71280734, compound

Product 1

HCID 71280663HCID 71280663, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-7-(piperidin-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (92) (15.6 mg, 0.032 mmol) and Et3N (0.013 mL, 0.095 mmol) in dichloromethane (1 mL) was added methanesulfonyl chloride (0.0074 mL, 0.095 mmol) and stirred at room temperature for 1 hour. The crude product was purified by preparative HPLC to yield N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-7-(1-(methylsulfonyl)piperidin-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (F49). MS (m/z) 571.1 (M+1)+.

Workup

  1. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-e9d3883494ee4babaf489253b6a24fa6
Source dataset
uspto-grants-2015_12
Patent number
US09199981B2

Reaction notes

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