Acetyl chloride → HCID 178474988, compound

HRID 474380Notes

Reaction equation

HRID 474380 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C@@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12][N:13]2[C:17]3=[N:18][C:19]([NH:22][C:23]4[CH:24]=[CH:25][C:26]([CH3:33])=[C:27]([S:29]([NH2:32])(=[O:31])=[O:30])[CH:28]=4)=[N:20][CH:21]=[C:16]3[CH:15]=[N:14]2)[CH2:8][CH2:7]1>C1COCC1>[CH3:33][C:26]1[CH:25]=[CH:24][C:23]([NH:22][C:19]2[N:18]=[C:17]3[N:13]([CH2:12][C@@H:9]4[CH2:8][CH2:7][C@H:6]([NH:5][C:1](=[O:3])[CH3:2])[CH2:11][CH2:10]4)[N:14]=[CH:15][C:16]3=[CH:21][N:20]=2)=[CH:28][C:27]=1[S:29](=[O:31])(=[O:30])[NH2:32]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 178426360HCID 178426360, compound

Product 1

HCID 178474988HCID 178474988, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetyl chloride (0.027 mL, 0.38 mmol) was added to a 10 mL vial charged with 5-(1-((cis-4-aminocyclohexyl)methyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)-2-methylbenzenesulfonamide (0.15 g, 0.36 mmol, Example #C.1.1) and TEA (1 mL) in THF (4 mL). The reaction mixture was stirred at ambient temperature for about 2 h, then concentrated under reduced pressure. The crude product was purified by RP-HPLC (Table 2, Method b) to give N-(cis-4-((6-(4-methyl-3-sulfamoylphenylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)cyclohexyl)acetamide (0.021 g, 13%) as a white solid. LC/MS (Table 2, Method a) Rt=1.71 min; MS m/z: 458 (M+H)+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude product was purified by RP-HPLC (Table 2, Method b)

Sources & evidence

ORD record
ord-ad7f8fe6833b4aea8294c25647fa5f2f
Source dataset
uspto-grants-2014_01
Patent number
US08637529B2

Reaction notes

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