Acetyl chloride → HCID 66934049, compound

HRID 390910Notes

Reaction equation

HRID 390910 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[C:12]3[S:17][C:16]([CH2:18][N:19]4[CH2:24][CH2:23][N:22](S(C)(=O)=O)[CH2:21][CH2:20]4)=[CH:15][C:13]=3[N:14]=2)=[CH:5][N:4]=1.[C:35](Cl)(=[O:37])[CH3:36].CCN(CC)CC.O.C(Cl)Cl>C(Cl)Cl>[CH3:1][N:2]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[C:12]3[S:17][C:16]([CH2:18][N:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)=[CH:15][C:13]=3[N:14]=2)=[CH:5][N:4]=1)[C:35](=[O:37])[CH3:36]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 21908982Water methylene chlorideHCID 58233927HCID 58233927, compound

Product 1

HCID 66934049HCID 66934049, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-methyl-5-(4-morpholino-6-((4-N-methylsulfonylpiperazin-1-yl)methyl)thieno[3,2-d]pyrimidin-2-yl)pyridin-2-amine 195 (1 eq.) was stirred with acetyl chloride (1 eq.) and NEt3 (1 eq.) in dry CH2Cl2 (10 mL) at R.T. overnight. Water/CH2Cl2 work up then purification on silica yielded 196 (28%). NMR (CDCl3): 2.17 (s, 3H, CH3), 2.69-2.70 (m, 4H, 2×CH2), 2.81 (s, 3H, CH3), 3.31 (m, 4H, 2×CH2), 3.44 (s, 3H, CH3), 3.88-3.90 (m, 6H, 3×CH2), 4.04-4.07 (m, 4H, 2×CH2), 7.33 (s, H, ArH), 7.39 (m, H, ArH), 8.70 (dd, H, ArH, J=6.08 Hz, 2.3 Hz), 9.47 (d, H, ArH, J=2.12 Hz). MS: (ESI+): MH+ 546.34

Workup

  1. custompurification on silica

Sources & evidence

ORD record
ord-4ec508e8209d482ab75fcf444dbf563d
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

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