Dimethylamine → 5-{5-[3-(3-Dimethylamino-propoxy)-phenylamino]-2-methylphenyl}-2-methylsulfanyl-4-pyridin-3-yl-thiophene-3-carbonitrile

HRID 6857Notes

Reaction equation

HRID 6857 reaction equation
[C:1]([C:3]1[C:4]([C:33]2[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=2)=[C:5]([C:10]2[CH:11]=[C:12]([NH:17][C:18]3[CH:19]=[C:20]([CH:30]=[CH:31][CH:32]=3)[O:21][CH2:22][CH2:23][CH2:24]OS(C)(=O)=O)[CH:13]=[CH:14][C:15]=2[CH3:16])[S:6][C:7]=1[S:8][CH3:9])#[N:2].[CH3:39][NH:40][CH3:41].C(N(CC)CC)C.O>C(Cl)Cl>[CH3:39][N:40]([CH3:41])[CH2:24][CH2:23][CH2:22][O:21][C:20]1[CH:19]=[C:18]([NH:17][C:12]2[CH:13]=[CH:14][C:15]([CH3:16])=[C:10]([C:5]3[S:6][C:7]([S:8][CH3:9])=[C:3]([C:1]#[N:2])[C:4]=3[C:33]3[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=3)[CH:11]=2)[CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 962WaterHCID 8471TriethylamineHCID 86588175Methanesulfonic Acid 3-{3-[3-(4-cyano-5-methylsulfanyl-3-pyridin-3-yl-thiophene-2-yl)-4-methyl-phenylamino]-phenoxyl}-propyl Ester

Product 1

HCID 220190335-{5-[3-(3-Dimethylamino-propoxy)-phenylamino]-2-methylphenyl}-2-methylsulfanyl-4-pyridin-3-yl-thiophene-3-carbonitrileYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methanesulfonic acid 3-{3-[3-(4-cyano-5-methylsulfanyl-3-pyridin-3-yl-thiophene-2-yl)-4-methyl-phenylamino]-phenoxyl}-propyl ester (20 mg, 0.035 mmol) in DCM (1 mL) was added excess dimethylamine and excess triethylamine. The reaction was stirred at ambient temperature for 3 hours then water (2 ml) was added and the product extracted with DCM (3 mL×3). The combined organic layer were concentrated to afford the crude product as an oil. Purification by chromatography (2% MeOH—CH2Cl2) afforded the desired product (17 mg, 95%). 1H NMR (CDCl3): δ 8.6 (d, 1H), 8.5 (s, 1H), 8.1 (s, 1H), 7.7 (d, 1H), 7.4–7.0 (m, 4H), 7.0 (d, 1H), 6.5 (d, 1H), 4.1 (t, 2H), 2.9 (m, 2H), 2.7 (s, 3H), 2.6 (s, 6H), 2.1 (m, 2H), 1.6 (s, 3H).

Workup

  1. extractionthe product extracted with DCM (3 mL×3)
  2. concentrationThe combined organic layer were concentrated
  3. customto afford the crude product as an oil
  4. customPurification by chromatography (2% MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-9388568c90274f3dbf1e9cde00a3a358
Source dataset
uspto-grants-2006_08
Patent number
US07084159B2

Reaction notes

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