Acetyl chloride → HCID 59129222, compound

HRID 1991839Notes

Reaction equation

HRID 1991839 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][C:9]([NH:14][C:15]([C:17]3([C:20]4[CH:30]=[CH:29][C:23]5[O:24][C:25]([F:28])([F:27])[O:26][C:22]=5[CH:21]=4)[CH2:19][CH2:18]3)=[O:16])=[C:10]([F:13])[CH:11]=2)[CH:6]=[C:5]1[C:31]([CH3:34])([CH3:33])[CH3:32].CCN(CC)CC.[C:42](Cl)(=[O:44])[CH3:43]>CN(C=O)C>[C:42]([NH:1][CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][C:9]([NH:14][C:15]([C:17]3([C:20]4[CH:30]=[CH:29][C:23]5[O:24][C:25]([F:28])([F:27])[O:26][C:22]=5[CH:21]=4)[CH2:18][CH2:19]3)=[O:16])=[C:10]([F:13])[CH:11]=2)[CH:6]=[C:5]1[C:31]([CH3:34])([CH3:33])[CH3:32])(=[O:44])[CH3:43]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 59129249HCID 59129249, compound

Product 1

HCID 59129222HCID 59129222, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(1-(2-aminoethyl)-2-tert-butyl-6-fluoro-1H-indol-5-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropane-carboxamide (47 mg, 0.10 mmol) and Et3N (28 μL, 0.20 mmol) in DMF (1 mL) was added acetyl chloride (7.1 μL, 0.10 mmol). The mixture was stirred at room temperature for 1 h before being filtered and purified by reverse phase HPLC (10-99% CH3CN/H2O) to yield N-(1-(2-acetamidoethyl)-2-tert-butyl-6-fluoro-1H-indol-5-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide. 1H NMR (400 MHz, DMSO-d6) δ 8.35 (s, 1H), 8.15 (t, J=5.9 Hz, 1H), 7.53 (s, 1H), 7.43-7.31 (m, 4H), 6.17 (s, 1H), 4.22 (m, 2H), 3.30 (m, 2H), 1.85 (s, 3H), 1.47 (m, 2H), 1.41 (s, 9H), 1.13 (m, 2H). HPLC ret. time 2.06 min, 10-99% CH3CN, 3 min run; ESI-MS 516.4 m/z (M+H+).

Workup

  1. filtrationbefore being filtered
  2. custompurified by reverse phase HPLC (10-99% CH3CN/H2O)

Sources & evidence

ORD record
ord-419af3a50f84491f94484e75c0fdc7d0
Source dataset
uspto-grants-2010_01
Patent number
US07645789B2

Reaction notes

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