Methanol → HCID 11568604, compound

HRID 2375829Notes

Reaction equation

HRID 2375829 reaction equation
Cl.Cl.Cl.[NH:4]1[C:12]2[C:7](=[CH:8][C:9]([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:10][CH:11]=2)[CH:6]=[N:5]1.[C:29]1([CH2:35][C:36](Cl)=[O:37])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.CCN(C(C)C)C(C)C.CO>ClCCl>[NH:4]1[C:12]2[C:7](=[CH:8][C:9]([NH:13][C:14]3[C:15]4[CH:22]=[C:21]([C:23]5[CH2:24][CH2:25][N:26]([C:36](=[O:37])[CH2:35][C:29]6[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=6)[CH2:27][CH:28]=5)[NH:20][C:16]=4[N:17]=[CH:18][N:19]=3)=[CH:10][CH:11]=2)[CH:6]=[N:5]1

Participants

6

Reactant 4

HCID 887MethanolHCID 7679Phenylacetyl chlorideHCID 81531DiisopropylethylamineHCID 69275332HCID 69275332, compound

Product 1

HCID 11568604HCID 11568604, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1H-indazol-5-yl)-[6-(1,2,3,6-tetrahydropyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amine tri-hydrochloride (73.6 mg, 0.2 mmol) and phenylacetyl chloride (31 mg, 0.2 mmol) in dichloromethane (1.5 mL) was added i-Pr2NEt (0.1 mL). The resulting mixture was stirred at rt for 3 h. MeOH (0.3 mL) was added to quench the reaction. Solvents were removed and the residue was dissolved in DMF (≈2 mL), which was purified by mass-directed HPLC to obtain the title compound. 1H-NMR (DMSO-d6, 400 MHz): δ=2.34 (m, 2H), 3.72 (t, J=5.6 Hz, 2H), 3.80 (d, J=17.6 Hz, 2H), 4.21 (d, J=35.6 Hz, 2H), 6.40 (s, 1H), 6.73 (d, J=38.4 Hz, 1H), 7.22-7.34 (m, 4H), 7.51 (d, J=8.8 Hz, 1H), 7.63 (m, 1H), 8.04 (s, 1H), 8.25 (d, J=4.4 Hz, 1H), 8.37 (t, J=7.2 Hz, 1H), 9.33 (d, J=13.6 Hz, 1H), 11.92 (d, J=14.8 Hz, 1H), 12.97 (s, 1H). MS (ES+): m/z 450.07 [MH+]. HPLC: tR=2.17 min (ZQ2000, polar—5 min).

Workup

  1. customto quench
  2. customthe reaction
  3. customSolvents were removed
  4. dissolutionthe residue was dissolved in DMF (≈2 mL)
  5. customwhich was purified by mass-directed HPLC

Sources & evidence

ORD record
ord-e1cfe45b3be74bd0b113c6079074f221
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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