2-(Dimethylamino)acetyl chloride → HCID 72520650, compound

HRID 2121998Notes

Reaction equation

HRID 2121998 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[C:11](=[C:14]2[N:22]([CH3:23])[C:21]3[CH2:20][CH2:19][NH:18][CH2:17][C:16]=3[S:15]2)[S:10][C:9]1=[N:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][C:32]=1[NH:33][CH2:34][CH3:35])[C:28]#[N:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:36][N:37]([CH2:39][C:40](Cl)=[O:41])[CH3:38]>C(Cl)(Cl)Cl>[CH2:1]([N:8]1[C:12](=[O:13])[C:11](=[C:14]2[N:22]([CH3:23])[C:21]3[CH2:20][CH2:19][N:18]([C:40](=[O:41])[CH2:39][N:37]([CH3:38])[CH3:36])[CH2:17][C:16]=3[S:15]2)[S:10][C:9]1=[N:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][C:32]=1[NH:33][CH2:34][CH3:35])[C:28]#[N:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70103442-(Dimethylamino)acetyl chlorideHCID 72639902HCID 72639902, compound

Product 1

HCID 72520650HCID 72520650, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To the product of Example 183 in CHCl3 was added N,N-dimethylaminoacetyl chloride and TEA. After 4 h the product mixture was concentrated and chromatographed (silica gel, 0-40% EtOAc/Hex) to yield the title compound. 1H-NMR (CDCl3): δ 7.39-7.44 (2H, m), 7.33 (2H, m), 7.23-7.30 (2H m), 7.19 (1H, br s), 6.47 (1H, d), 5.15 (2H, s), 4.61 (1H, br s), 4.51 (1H, br s), 4.27 (1H, m), 3.92 (2H, m), 3.64 (3H, br s), 3.22 (1H, br s), 3.16 (1H, br s), 2.99 (2H, m), 2.63 (1H, br s), 2.56 (1H, br s), 2.31 (3H, s), 2.28 (3H, s), 1.01 (3H, t); MS(ESI): 588 (MH+).

Workup

  1. concentrationAfter 4 h the product mixture was concentrated
  2. customchromatographed (silica gel, 0-40% EtOAc/Hex)

Sources & evidence

ORD record
ord-517a4dd45d9b4308b92b6b80944323d0
Source dataset
uspto-grants-2004_02
Patent number
US06696473B2

Reaction notes

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