1,2-Dichloroethane → 1-{4-[4-(Benzothiazol-6-ylamino)-7h-pyrrolo[2,3-d]-pyrimidin-6-yl]-3,6-dihydro-2h-pyridin-1-yl}-2-pyridin-3-ylethanone

HRID 2375831Notes

Reaction equation

HRID 2375831 reaction equation
Cl.Cl.Cl.[S:4]1[C:8]2[CH:9]=[C:10]([NH:13][C:14]3[C:15]4[CH:22]=[C:21]([C:23]5[CH2:24][CH2:25][NH:26][CH2:27][CH:28]=5)[NH:20][C:16]=4[N:17]=[CH:18][N:19]=3)[CH:11]=[CH:12][C:7]=2[N:6]=[CH:5]1.Cl.[N:30]1[CH:35]=[CH:34][CH:33]=[C:32]([CH2:36][C:37](O)=[O:38])[CH:31]=1.C(Cl)CCl.C(N(CC)C(C)C)(C)C>CN(C=O)C>[S:4]1[C:8]2[CH:9]=[C:10]([NH:13][C:14]3[C:15]4[CH:22]=[C:21]([C:23]5[CH2:24][CH2:25][N:26]([C:37](=[O:38])[CH2:36][C:32]6[CH:31]=[N:30][CH:35]=[CH:34][CH:33]=6)[CH2:27][CH:28]=5)[NH:20][C:16]=4[N:17]=[CH:18][N:19]=3)[CH:11]=[CH:12][C:7]=2[N:6]=[CH:5]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 27237243-Pyridineacetic acid, hydrochloride (1:1)HCID 69274170Benzothiazol-6-yl-[6-(1,2,3,6-tetrahydropyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amine trihydrochloride

Product 1

HCID 115183831-{4-[4-(Benzothiazol-6-ylamino)-7h-pyrrolo[2,3-d]-pyrimidin-6-yl]-3,6-dihydro-2h-pyridin-1-yl}-2-pyridin-3-ylethanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of benzothiazol-6-yl-[6-(1,2,3,6-tetrahydropyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amine tri-HCl (137 mg, 0.300 mmol), 3-pyridinylacetic acid-HCl (78.1 mg, 0.450 mmol), and EDC (115 mg, 0.600 mmol) in DMF (1 mL) was added N,N-diisopropylethylamine (0.261 mL, 1.50 mmol). The mixture became a clear solution after being stirred for a few minutes and was stirred overnight. The products, which precipitated from the solution during the reaction, were collected by filtration, washed with dichloromethane (2×1 mL), and dried in vacuo to afford the title compound as a white solid. 1H-NMR (DMSO-d6, 400 MHz): δ=2.73 (s, 2H), 2.89 (s, 2H), 3.78 (dt, J=4.0, 18.8 Hz, 2H), 3.86 (d, J=20 Hz, 2H), 4.19 (s, 1H), 4.33 (s, 1H), 6.45 (d, J=5.2 Hz, 1H), 6.84 (d, J=16.8 Hz, 1H), 7.33-7.36 (m, 1H), 7.65 (t, J=8.0 Hz, 1H), 7.87 (dt, J=2.0, 8.0 Hz, 1H), 7.95 (s, 1H), 8.04 (d, J=9.2 Hz, 1H), 8.34 (d, J=3.6 Hz, 1H), 8.44-8.48 (m, 1H), 8.92 (s, 1H), 9.24 (s, 1H), 9.62 (d, J=7.6 Hz, 1H). MS (ES+): m/z 467.94 [MH+]. HPLC: tR=1.98 min (ZQ2000, polar—5 min).

Workup

  1. stirringwas stirred overnight
  2. customThe products, which precipitated from the solution during the reaction
  3. filtrationwere collected by filtration
  4. washwashed with dichloromethane (2×1 mL)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-1ac194b74f694b3abbe2b9cda6bf2021
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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