1,2-Dichloroethane → 6-[1-(2,2-Dimethyl-3-oxopropanoyl)-1,2,3,6-tetra-hydropyridin-4-yl]-N-1,3-benzothiazol-6-yl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 2375835Notes

Reaction equation

HRID 2375835 reaction equation
[OH:1][CH2:2][C:3]([CH3:32])([CH3:31])[C:4]([N:6]1[CH2:11][CH:10]=[C:9]([C:12]2[NH:30][C:15]3[N:16]=[CH:17][N:18]=[C:19]([NH:20][C:21]4[CH:29]=[CH:28][C:24]5[N:25]=[CH:26][S:27][C:23]=5[CH:22]=4)[C:14]=3[CH:13]=2)[CH2:8][CH2:7]1)=[O:5].C(Cl)CCl.CCOC(C)=O>CS(C)=O>[CH3:31][C:3]([CH3:32])([CH:2]=[O:1])[C:4]([N:6]1[CH2:7][CH:8]=[C:9]([C:12]2[NH:30][C:15]3[N:16]=[CH:17][N:18]=[C:19]([NH:20][C:21]4[CH:29]=[CH:28][C:24]5[N:25]=[CH:26][S:27][C:23]=5[CH:22]=4)[C:14]=3[CH:13]=2)[CH2:10][CH2:11]1)=[O:5]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 8857Ethyl AcetateHCID 587098916-[1-(3-Hydroxy-2,2-dimethylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-1,3-benzothiazol-6-yl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Product 1

HCID 587100686-[1-(2,2-Dimethyl-3-oxopropanoyl)-1,2,3,6-tetra-hydropyridin-4-yl]-N-1,3-benzothiazol-6-yl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 6-[1-(3-hydroxy-2,2-dimethylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-1,3-benzothiazol-6-yl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (Example 110) (150 mg, 0.33 mmol) in DMSO (4 mL) was added EDC (190 mg, 1 mmol). The reaction mixture stirred at rt for 5 h. The mixture was taken up in a large amount of EtOAc and extracted with water. The combined organic extracts were dried over sodium sulfate and concentrated in vacuo, which afforded the title compound as a yellow solid. MS (ES+): m/z: 446.93 (100) [MH+]. HPLC: tr=2.53 min (ZQ2000: polar—5 min). 1H NMR (400 MHz, DMSO-d6): δ=1.37 (s, 6H) 3.39-3.69 (m, 3H), 3.70-4.22 (m, 3H), 6.21 (bs, 1H), 6.82 (s, 1H), 6.84 (d, J=1.6 Hz, 1H), 7.87 (dd, J=1.6, 8.8 Hz, 1H), 8.03 (d, J=8.8 Hz, 1H), 8.34 (s, 1H), 8.91 (d, J=2.0 Hz, 1H), 9.23 (s, 1H), 9.62 (s, 1H), 12.03 (s, 1H).

Workup

  1. extractionextracted with water
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. concentrationconcentrated in vacuo, which

Sources & evidence

ORD record
ord-542947fdbcbc4e0e80382723cffa9db2
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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