Acetyl chloride → HCID 74928775, compound

HRID 523310Notes

Reaction equation

HRID 523310 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH:5]1([C:11]2[C:12]3[CH:13]=[CH:14][C:15]4[C:16](=[O:57])[NH:17][CH2:18][CH2:19][CH:20]=[CH:21][CH2:22][CH2:23][NH:24][C:25](=[O:56])[CH2:26][N:27]([C:54]=3[CH:55]=4)[C:28]=2[C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37]3[CH:42]=[C:41]([NH2:43])[CH:40]=[CH:39][C:38]=3[N:44]3[CH2:49][CH2:48][N:47]([S:50]([CH3:53])(=[O:52])=[O:51])[CH2:46][CH2:45]3)=[CH:31][CH:30]=2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.CCN(C(C)C)C(C)C>C(Cl)(Cl)Cl>[CH:5]1([C:11]2[C:12]3[CH:13]=[CH:14][C:15]4[C:16](=[O:57])[NH:17][CH2:18][CH2:19][CH:20]=[CH:21][CH2:22][CH2:23][NH:24][C:25](=[O:56])[CH2:26][N:27]([C:54]=3[CH:55]=4)[C:28]=2[C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37]3[CH:42]=[C:41]([NH:43][C:1](=[O:3])[CH3:2])[CH:40]=[CH:39][C:38]=3[N:44]3[CH2:45][CH2:46][N:47]([S:50]([CH3:53])(=[O:51])=[O:52])[CH2:48][CH2:49]3)=[CH:31][CH:30]=2)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 7492875217-Cyclohexyl-18-[4-[2-(4 methanesulfonylpiperazin-1-yl)-5-amino-benzyloxy]phenyl]-1,4,11-triazatricyclo[11.5.2.016,19]icosa-7,13 (20),14,16(19),17-pentaene-3,12-dione

Product 1

HCID 74928775HCID 74928775, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Acetyl chloride (4 μL, 0.057 mmol) was added under nitrogen to a solution of 4 (38 mg, 0.051 mmol) and N,N′-diisopropylethylamine (DIPEA; 8.7 μL, 0.062 mmol) in CHCl3 (2 mL). After 12 h, the reaction mixture was successively partitioned between CHCl3 and diluted NaHCO3, dried (Na2SO4) and evaporated. The residue was purified by column chromatography to give 25 mg (61.7%) of the title product 5 as a white powder: m/z=782 (M+H)+. NMR (DMSO-d6): δ (ppm) 1.19-1.35 (m, 4H), 1.68-1.77 (m, 4H), 1.90 (m, 2H), 2.02 (s, 3H, COCH3), 2.18 (m, 2H), 2.33 (m, 2H), 2.50 (m, 1H), 2.75 (m, 2H), 2.92 (s, 3H, SO2CH3), 2.96 (m, 2H), 3.33 (m, 8H), 4.43 (s, 2H, CH2CONH), 5.22 (s, 2H, OCH2), 5.35 (m, 1H), 5.53 (m, 1H), 7.17-7.20 (m, 3H), 7.39-7.60 (m, 5H), 7.69-7.79 (m, 2H), 7.86 (broad s, 1H, NH), 8.33+8.56 (m, 1H, NH), 9.95 (s, 1H, NH).

Workup

  1. customthe reaction mixture was successively partitioned between CHCl3 and diluted NaHCO3
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-230e56ce65b94214840b1164cc1b5c8e
Source dataset
uspto-grants-2016_05
Patent number
US09334282B2

Reaction notes

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