Dimethylamine, hydrochloride → HCID 57933144, compound

HRID 1432183Notes

Reaction equation

HRID 1432183 reaction equation
[Cl:1][C:2]1[S:27][C:5]2[N:6]=[CH:7][N:8]=[C:9]([NH:10][CH:11]3[CH2:16][CH2:15][N:14]([CH2:17][C:18]4[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=4)[C:21](O)=[O:22])[CH2:13][CH2:12]3)[C:4]=2[CH:3]=1.Cl.[CH3:29][NH:30][CH3:31].CCN(C(C)C)C(C)C>S(Cl)(Cl)=O.C(Cl)Cl>[Cl:1][C:2]1[S:27][C:5]2[N:6]=[CH:7][N:8]=[C:9]([NH:10][CH:11]3[CH2:16][CH2:15][N:14]([CH2:17][C:18]4[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=4)[C:21]([N:30]([CH3:31])[CH3:29])=[O:22])[CH2:13][CH2:12]3)[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 11632767HCID 11632767, compound

Product 1

HCID 57933144HCID 57933144, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

3-((4-(6-Chlorothieno[2,3-d]pyrimidin-4-ylamino)piperidin-1-yl)methyl)benzoic acid (104 mg, 0.26 mmol) was heated in 3 mL of thionylchloride at 80° C. for 3 h. The reaction was cooled to room temperature and the thionylchloride was removed under reduced pressure. The residue obtained was dissolved in 25 mL of DCM followed by addition of dimethylamine hydrochloride (63 mg, 0.77 mmol) and DIEA (200 mg, 1.55 mmol). The reaction was allowed to stir at room temperature for 16 h and extracted with 25 mL of water. The DCM layer was dried over Na2SO4 and evaporated under reduced pressure; the crude product was purified by silica chromatography in 5% MeOH-DCM to obtain 67 mg of product in 60% yield. 1H NMR (400 MHz, CDCl3) δ 8.43 (s, 1H), 7.33 (m, 4H), 7.03 (s, 1H), 5.03 (d, 1H), 4.17 (m, 1H), 3.55 (s, 2H), 3.13 (s, 3H), 2.99 (s, 3H), 2.86 (d, 2H), 2.22 (t, 2H), 2.19 (d, 2H), 1.55 (dq, 2H); MS (ESI) m/z: Calculated for C21H25ClN5OS, 430.15; Observed: 430.2 (M++1).

Workup

  1. customthe thionylchloride was removed under reduced pressure
  2. customThe residue obtained
  3. extractionextracted with 25 mL of water
  4. dry with materialThe DCM layer was dried over Na2SO4
  5. customevaporated under reduced pressure
  6. customthe crude product was purified by silica chromatography in 5% MeOH-DCM

Sources & evidence

ORD record
ord-110b4be78d77436e8a865afc59ae1c8d
Source dataset
uspto-grants-2009_11
Patent number
US07612078B2

Reaction notes

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