HCID 58710091, compound → HCID 58710055, compound

HRID 2375884Notes

Reaction equation

HRID 2375884 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:9]2[S:13][CH:12]=[N:11][CH:10]=2)[CH:3]=1.Cl[C:15]1[N:16]=[CH:17][C:18]2[CH:23]=[C:22]([C:24]3[CH2:25][CH2:26][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:28][CH:29]=3)[NH:21][C:19]=2[N:20]=1>C(O)CCC>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:17]2[C:18]3[CH:23]=[C:22]([C:24]4[CH2:25][CH2:26][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:28][CH:29]=4)[NH:21][C:19]=3[N:20]=[CH:15][N:16]=2)=[CH:3][C:4]=1[C:9]1[S:13][CH:12]=[N:11][CH:10]=1

Participants

4

Reactant 2

HCID 58710091HCID 58710091, compoundHCID 86607818HCID 86607818, compound

Product 1

HCID 58710055HCID 58710055, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

4-Amino-2-thiazol-5-ylphenol (70.0 mg, 0.364 mmol) was added to a solution of tert-butyl 4-(chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylate (192 mg, 0.546 mol) in n-butanol (2.0 mL). The reaction was stirred at 120° C. for 14 h. The solvent was removed and the residue was dissolved in DMF. The DMF solution was filtered and purified by HPLC to give the title compound. 1H-NMR (DMSO-d6, 400 MHz): δ=1.43 (s, 9H), 2.46 (m, 2H), 3.56 (t, J=5.6 Hz, 2H), 4.04 (s, 2H), 6.38 (s, br, 1H), 6.70 (s, 1H), 6.97 (d, J=8.8 Hz, 1H), 7.70 (dd, J=2.4, 8.8 Hz, 1H), 8.07 (d, J=2.4 Hz, 1H), 8.22 (s, 1H), 8.32 (s, 1H), 9.05 (s, 1H), 9.23 (s, 1H), 10.25 (s, br, 1H), 11.88 (s, 1H). MS (ES+): m/z 490.94 (MH+). HPLC: tR=2.51 min (ZQ2000, polar—5 min).

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in DMF
  3. filtrationThe DMF solution was filtered
  4. custompurified by HPLC

Sources & evidence

ORD record
ord-0b2b27c6e2654e0aa219c0a1c3e29d52
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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