Trifluoroacetic acid → HCID 58710011, compound

HRID 2375875Notes

Reaction equation

HRID 2375875 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[NH:23][C:17]3[N:18]=[CH:19][N:20]=[C:21](Cl)[C:16]=3[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:24][C:25]1[CH:26]=[C:27]([NH2:38])[CH:28]=[C:29]([N:31]2[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]2)[CH:30]=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+].C(OC(OC(OC(C)(C)C)=O)=O)(C)(C)C>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[NH:23][C:17]3[N:18]=[CH:19][N:20]=[C:21]([NH:38][C:27]4[CH:28]=[C:29]([N:31]5[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]5)[CH:30]=[C:25]([Cl:24])[CH:26]=4)[C:16]=3[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 90495Di-tert-butyl dicarbonateHCID 516892Sodium BicarbonateHCID 58709797tert-butyl 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3,6-dihydropyridine-1(2H)-carboxylateHCID 58709802HCID 58709802, compound

Product 1

HCID 58710011HCID 58710011, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

A mixture of 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (88.0 mg, 0.263 mmol), 3-chloro-5-(4-methylpiperazin-1-yl)-phenylamine (71.2 mg, 0.316 mmol), trifluoroacetic acid (203 μL, 2.63 mmol), and DMF (2 mL) was stirred in a sealed tube at 70° C. for 18 h. The mixture was concentrated in vacuo, sodium bicarbonate (221 mg, 2.63 mmol), di-tert-butyldicarbonate (86.1 mg, 0.394 mmol), and DMF (2 mL) were added to the residue, and the resulting mixture was stirred at rt under N2 for 16 h. After that time, the mixture was filtered, and the filtrate was concentrated in vacuo and submitted for MS-directed purification. One obtained the title compound as light-brown solid. 1H NMR (CD3OD, 400 MHz): δ=1.50 (s, 9H), 2.57 (brs, 2H), 2.86 (s, 3H), 3.29 (brs, 4H), 3.46 (brs, 4H), 3.67 (brs, 2H), 4.13 (brs, 2H), 6.29 (brs, 1H), 6.68 (s, 1H), 6.74 (s 1H), 7.44 (s, 1H), 7.47 (s, 1H), 8.28 (s, 1H). M (ES+): m/z 523.99/525.95(100/40) [MH+]. HPLC: tR (polar—5 mins)=2.28 min (ZQ2000, polar—5 min).

Workup

  1. additionwere added to the residue
  2. stirringthe resulting mixture was stirred at rt under N2 for 16 h
  3. filtrationAfter that time, the mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customsubmitted for MS-directed purification

Sources & evidence

ORD record
ord-52ea66247d914d1a91a7aa1bc24ae86c
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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